HCID 69217498, compound → HCID 69218877, compound

HRID 1394632Notes

Reaction equation

HRID 1394632 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH:4]=[C:5]([C:7]1[CH:31]=[CH:30][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[O:26]COC)[C:9]=2[CH:8]=1)[CH3:6]>CO.Cl>[CH3:1][O:2][C:3](=[O:32])[CH:4]=[C:5]([C:7]1[CH:31]=[CH:30][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[OH:26])[C:9]=2[CH:8]=1)[CH3:6]

Participants

4

Reactant 1

HCID 69217498HCID 69217498, compound

Product 1

HCID 69218877HCID 69218877, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

3-[3-(3,5-Di-iso-propyl-2-methoxymethoxy-phenyl)-benzo[b]thien-5-yl]-but-2-enoic acid methyl ester (15 mg, 0.033 mmol) was dissolved in methanol (5 ml) and 2 drops of concentrated HCl was added. This mixture was stirred at ambient temperature for 4 h then concentrated in vacuo. The residue was passed over a silica gel plug (50% ethyl acetate in hexane) to yield a quatitative amount of 3-[3-(2-hydroxy-3,5-di-iso-propylphenyl)-benzo[b]thien-5-yl]-but-2-enoic acid methyl ester as a white solid which was used without further purification. 1H NMR (250 MHz, CDCl3): δ 7.96 (d, 1H, J=11.2), 7.77 (d, 1H, J=0.6), 7.75-7.61 (m, 2H), 7.18 (d, 1H, J=3.1), 7.05 (d, 1H, J=3.1), 6.20 (d, 1H, J=1.2), 5.05 (bs, 1H), 3.77 (s, 3H), 3.38 (m, 1H), 2.94 (m, 1H), 2.62 (d, 3H, J=1.2), 1.36 (s, 3H), 1.34 (s, 3H), 1.33 (s, 3H), 1.31 (s 3H). MS [EI+] 426 (M+H2O)+, [EI−] 407 (M−1)−.

Workup

  1. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-df1916f542274c269842336a0c5f8572
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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