Water → HCID 69219674, compound

HRID 1394634Notes

Reaction equation

HRID 1394634 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH:4]=[C:5]([C:7]1[CH:28]=[CH:27][C:10]2[S:11][CH:12]=[C:13]([C:14]3[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[CH:17]=[C:16]([CH:23]([CH3:25])[CH3:24])[C:15]=3[OH:26])[C:9]=2[CH:8]=1)[CH3:6].I[CH3:31].[F-].[Cs+].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:29])[CH:4]=[C:5]([C:7]1[CH:28]=[CH:27][C:10]2[S:11][CH:12]=[C:13]([C:14]3[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[CH:17]=[C:16]([CH:23]([CH3:24])[CH3:25])[C:15]=3[O:26][CH3:31])[C:9]=2[CH:8]=1)[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 25953Cesium fluorideHCID 69218877HCID 69218877, compound

Product 1

HCID 69219674HCID 69219674, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[3-(2-Hydroxy-3,5-di-iso-propylphenyl)-benzo[b]thien-5-yl]-but-2-enoic acid methyl ester (100 mg, 0.24 mmol) was dissolved in DMF (5 ml), and iodomethane (0.0183 ml, 0.29 mmol) and cesium fluoride (149 mg, 0.98 mmol) were added to this solution. The reaction was stirred at ambient temperature under nitrogen overnight, then water (2 ml) was added and the mixture extracted with ethyl acetate (2×5 mL). The combined organics were washed with brine, then dried over MgSO4 and concentrated in vacuo to yield 3-[3-(3,5-di-iso-propyl-2-methoxyphenyl)-benzo[b]thien-5-yl]but-2-enoic acid methyl ester as a pale yellow solid (101 mg, 98%). 1H NMR (250 MHz, CDCl3): δ 7.85 (d, 1H, J=6.2), 7.80 (s, 1H), 7.46 (s, 1H), 7.40 (dd, 1H, J=0.6, J=8.8), 7.09 (d, 1H, J=1.2), 7.03 (d, 1H, J=1.2), 6.12 (d, 1H, J=0.6), 3.65 (s, 3H), 3.32 (m, 1H), 3.18 (s, 3H), 2.85 (m, 1H), 2.53 (d, 3H, J=0.6), 1.24 (s, 3H), 1.22 (s, 6H), 1.18 (s, 3H).

Workup

  1. extractionthe mixture extracted with ethyl acetate (2×5 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-59ddb8279841460ea06b69b1b01a4924
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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