benzyl tetrahydrofuran-3-carboxylate synthesis
- Product Name:benzyl tetrahydrofuran-3-carboxylate
- CAS Number:1445651-64-8
- Molecular formula:C12H14O3
- Molecular Weight:206.24
89364-31-8
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100-39-0
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1445651-64-8
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Yield:1445651-64-8 98%
Reaction Conditions:
with potassium carbonate in N,N-dimethyl-formamide at 100; for 18 h;
Steps:
a a) Tetrahydro-furan-3-carboxylic acid benzyl ester
a)
Tetrahydro-furan-3-carboxylic acid benzyl ester
A solution of tetrahydro-furan-3-carboxylic acid (CAS registry 89364-31-8) (4.00 g, 34.40 mmol) in DMF (20 ml) was treated with K2CO3 (9.52 g, 68.9 mmol) and benzyl bromide (CAS registry 100-39-0) (8.18 ml, 68.9 mmol) at 100° C. for 18 h.
The mixture was cooled down to rt, diluted with EtOAc, washed with water and brine.
Combined organic layers were dried over MgSO4, concentrated and purified by flash chromatography on silica gel (cyclohexane/EtOAc 92:8 to 34:66) to afford the title compound as colourless oil (6.93 g, 98% yield)
HPLC RtM2=0.94 min; ESIMS: 207 [(M+H)+].
1H NMR (400 MHz, CDCl3): δ 7.50-7.26 (m, 5H), 5.17 (m, 2H), 4.05-3.75 (m, 4H), 3.29-3.05 (m, 1H), 2.36-2.09 (m, 2H).
References:
US2013/165436,2013,A1 Location in patent:Paragraph 0796; 0797; 07968; 0799
