Cesium carbonate → 4-(4-Methanesulfonyl-phenoxy)-benzofuran-6-carboxylic acid ethyl ester

HRID 1643553Notes

Reaction equation

HRID 1643553 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](C)[CH2:11][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)C2C=COC=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:24])=[O:23])=[CH:20][CH:21]=2)[C:8]2[CH:11]=[CH: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 11344757Ethyl 4-hydroxybenzofuran-6-carboxylateHCID 595604376-(4-Methanesulfonyl-phenoxy)-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester

Product 1

HCID 595601744-(4-Methanesulfonyl-phenoxy)-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 (180 mg, 1.03 mmol), Cs2CO3 (630 mg, 1.93 mmol), and 4-hydroxy-benzofuran-6-carboxylic acid ethyl ester (8a) (199 mg, 0.97 mmol). Purification by flash column chromatography eluting with 15% EtOAc in hexanes gave a pale yellow oil (261 mg, 75% yield). 1H NMR (400 MHz, CDCl3) δ 8.13 (s, 1 H) 7.91 (s, 2 H) 7.74 (s, 1 H) 7.65 (s, 1 H) 7.13 (s, 2 H) 6.66 (s, 1 H) 4.41 (s, 2 H) 3.08 (s, 3 H) 1.42 (s, 3 H); LCMS for C18H1606S m/z 383.00 (M+Na)+.

Workup

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

Sources & evidence

ORD record
ord-442bfa199937494d8ffed3487bead1d9
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

Loading…