Cesium carbonate → 4-(4-Methanesulfonyl-phenoxy)-2,3-dihydro-benzofuran-6-carboxylic acid ethyl ester

HRID 1643552Notes

Reaction equation

HRID 1643552 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])C[C:10]=12)=[O:4].[CH3:26]S(C1C=CC(F)=CC=1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+].C(OC(C1C=C(O)C2CCOC=2C=1)=O)C>>[CH2:1]([O:2][C:3]([C:5]1[CH:6]=[C:7]([O:15][C:16]2[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:23])=[O:24])=[CH:20][CH:21]=2)[C:8]2[CH2:14][CH2:12][O:13][C:9]=2[CH:10]=1)=[O:4])[CH3:26]

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 59559879Ethyl 4-hydroxy-2,3-dihydrobenzofuran-6-carboxylateHCID 595604376-(4-Methanesulfonyl-phenoxy)-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester

Product 1

HCID 595603284-(4-Methanesulfonyl-phenoxy)-2,3-dihydro-benzofuran-6-carboxylic acid ethyl ester

Procedure

The title compound was prepared in a similar manner as described for Intermediate 1f, from 4-fluorophenyl methyl sulfone (285 mg, 1.64 mmol), Cs2CO3 (997 mg, 3.06 mmol), and 4-hydroxy-2,3-dihydro-benzofuran-6-carboxylic acid ethyl ester (8b) (315 mg, 1.51 mmol). Purification by column chromatography eluting with 10-20% EtOAC in hexanes gave a pale yellow oil (199 mg, 36% yield). 1H NMR (400 MHz, CDCl3) δ 7.90-7.97 (m, 2 H) 7.34 (d, J=4.29 Hz, 1 H) 7.24-7.29 (m, 1 H) 7.07-7.13 (m, 2 H) 4.67 (m, 2 H) 4.32-4.39 (m, 2 H) 3.09-3.14 (m, 2 H) 3.06-3.09 (m, 3 H) 1.34-1.42 (m, 3 H); LCMS for C18H18O6S m/z 385.00 (M+Na)+.

Workup

  1. customPurification by column chromatography
  2. washeluting with 10-20% EtOAC in hexanes

Sources & evidence

ORD record
ord-18e8a92d15824c53988c3ad334c3797e
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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