(6-Hydroxy-5-methyl-benzo[b]thiophen-3-yl)-acetic acid methyl ester → {5-Methyl-6-[2-(4-trifluoromethyl-benzyloxy)-benzyloxy]-benzo[b]-thiophen-3-yl}-acetic acid

HRID 1814180Notes

Reaction equation

HRID 1814180 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][C:5]1[C:6]2[CH:13]=[C:12]([CH3:14])[C:11]([OH:15])=[CH:10][C:7]=2[S:8][CH:9]=1.[F:17][C:18]([F:36])([F:35])[C:19]1[CH:34]=[CH:33][C:22]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH2:31]O)=[CH:21][CH:20]=1.COC(=O)CC1C2C=CC=C(O)C=2SC=1>>[CH3:14][C:12]1[C:11]([O:15][CH2:31][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[O:24][CH2:23][C:22]2[CH:33]=[CH:34][C:19]([C:18]([F:17])([F:35])[F:36])=[CH:20][CH:21]=2)=[CH:10][C:7]2[S:8][CH:9]=[C:5]([CH2:4][C:3]([OH:2])=[O:16])[C:6]=2[CH:13]=1

Participants

4

Reactant 3

HCID 20770860(6-Hydroxy-5-methyl-benzo[b]thiophen-3-yl)-acetic acid methyl esterHCID 20770870HCID 20770870, compoundHCID 22279996[2-(4-Trifluoromethyl-benzyloxy)-phenyl]-methanol

Product 1

HCID 22504750{5-Methyl-6-[2-(4-trifluoromethyl-benzyloxy)-benzyloxy]-benzo[b]-thiophen-3-yl}-acetic acidYield 43%

Procedure

The title compound was prepared using compound 78C from the preceding step and compound 7A in a manner analogous to compound 77B. Thus, recrystallization from methanol afforded 0.42 g (43% yield) of the title compound as a cream-colored powder, mp 108-109° C. Calc for C27H23F3O4S: C, 64.79; H, 4.63; found: C, 64.64; H, 4.46. Step 5. Preparation of {5-Methyl-6-[2-(4-trifluoromethyl-benzyloxy)-benzyloxy]-benzo[b]thiophen-3-yl}-acetic acid (Compound 78)

Workup

  1. customThe title compound was prepared
  2. customThus, recrystallization from methanol

Sources & evidence

ORD record
ord-7b6c73ab37a743028c4cebd5a6ac4a83
Source dataset
uspto-grants-2005_04
Patent number
US06875780B2

Reaction notes

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