Dimethylformamide → HCID 69220380, compound

HRID 1394595Notes

Reaction equation

[H-].[Na+].C([C:6]1[S:10][C:9]2[C:11]([C:15]3[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:18]=[C:17]([CH:24]([CH3:26])[CH3:25])[C:16]=3[O:27][CH2:28][CH3:29])=[CH:12][CH:13]=[CH:14][C:8]=2[CH:7]=1)(=O)C.CN([CH:33]=[O:34])C>>[CH2:16]([O:27][C:33](=[O:34])[CH:6]=[C:7]([C:6]1[S:10][C:9]2[C:11]([C:15]3[CH:20]=[C:19]([CH:21]([CH3:22])[CH3:23])[CH:18]=[C:17]([CH:24]([CH3:26])[CH3:25])[C:16]=3[O:27][CH2:28][CH3:29])=[CH:12][CH:13]=[CH:14][C:8]=2[CH:7]=1)[CH3:8])[CH3:15]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 17952742HCID 17952742, compound

Product 1

HCID 69220380HCID 69220380, compoundYield 59%

Conditions

Temperature: 40 °C

Procedure

To a mixture of 38 mg (0.79 mmol) of NaH in 1 mL of dry DMF was added dropwise a solution of 148 mg (0.66 mmol, 0.13 mL) of triethylphosphonoacetate at 0° C. After 10 minutes, 125 mg of 2-acetyl-7-(2-ethoxy-3,5-diisopropylphenyl)-benzo[b]thiophene (diluted in 2 mL of dry DMF) was added slowly and the mixture is warmed-up to 40° C. After complexion of the reaction (TLC), and work-up, the crude ester was purified over a short pad of silica gel (eluent: ethyl acetate/hexane: 95/5) to afford 87 mg (0.193 mmol, yield=59%) of 3-[7-(2-ethoxy-3,5-diisopropylphenyl)-benzo[b]thien-2-yl]-but-2-enoic acid ethyl ester (ratio E/Z=85/15)1. 1H-NMR (CDCl3), δ: 7.73 (d, J=7.8 Hz, 1H), 7.60 (s, 1H), 7.45 (d, J=1.0 Hz, 1H), 7.43 (t, J=7.9 Hz, 1H), 7.17 (m, 2H), 6.29 (s, 1H), 4.19 (dd, J=14.5, 7.3 z, 2H), 3.44 (dt, J=13.7, 6.9 Hz, 1H), 3.36 (dd, J=14.0, 7.0 Hz, 2H), 2.92 (dt, J=13.7, 6.8 Hz, 1H), 2.66 (s, 3H), 1.28 (m, 12H), 0.90 (t, J=7.0 Hz, 3H).

Workup

customAfter complexion of the reaction (TLC)
customthe crude ester was purified over a short pad of silica gel (eluent: ethyl acetate/hexane: 95/5)

Sources & evidence

ORD record: ord-f530d393d90a4fe989ccd4d1b327b200
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348359B2

Reaction notes

Loading…