4-Hydroxy-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester → 4-(4-Methanesulfonyl-phenoxy)-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

HRID 1643556Notes

Reaction equation

HRID 1643556 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH:8]=[C:9]2[O:13][CH:12]([CH3:14])[CH2:11][C:10]=12)=[O:4].COC(C1C=C(O)C2CC(C)OC=2C=1)=O>>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:23])=[O:24])=[CH:18][CH:17]=2)[C:8]2[CH2:11][CH:12]([CH3:14])[O:13][C:9]=2[CH:10]=1)=[O:4]

Participants

3

Reactant 2

HCID 595600564-Hydroxy-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl esterHCID 595604376-(4-Methanesulfonyl-phenoxy)-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester

Product 1

HCID 595600764-(4-Methanesulfonyl-phenoxy)-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

Procedure

The title compound was prepared in a similar manner as described for Intermediate 1f, from 4-hydroxy-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (10c) (58 mg, 0.29 mmol). Purification by column chromatography eluting with 15-25% EtOAc in hexanes gave a pale yellow solid (65 mg, 64% yield). 1H NMR (400 MHz, CDCl3) δ 7.90-7.93 (m, 2 H) 7.23-7.26 (m, 2 H) 7.10 (s, 1 H) 7.07 (s, 1 H) 4.98-5.07 (m, 1 H) 3.89 (s, 3 H) 3.21 (dd, J=16.67, 8.84 Hz, 1 H) 3.07 (s, 3 H) 2.70 (dd, J=16.55, 7.45 Hz, 1 H) 1.48 (d, J=6.32 Hz, 3 H); LCMS for C18H18O6S m/z 385.10 (M+Na)+.

Workup

  1. customPurification by column chromatography
  2. washeluting with 15-25% EtOAc in hexanes

Sources & evidence

ORD record
ord-acc64229608c458d8d04216dd2a9f4d3
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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