Triethylamine → HCID 57810567, compound

HRID 2106467Notes

Reaction equation

HRID 2106467 reaction equation
[CH2:1]([C:3]([C:16]1[CH:29]=[CH:28][C:19]([O:20][CH2:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[C:18]([CH3:30])[CH:17]=1)([C:6]1[O:7][C:8]2[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:9]=2[CH:10]=1)[CH2:4][CH3:5])[CH3:2].CCN(CC)CC.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(Cl)Cl>[CH3:26][C:23]([CH3:25])([CH3:24])[C:22](=[O:27])[CH2:21][O:20][C:19]1[CH:28]=[CH:29][C:16]([C:3]([C:6]2[O:7][C:8]3[CH:14]=[C:13]([O:15][S:39]([CH3:38])(=[O:41])=[O:40])[CH:12]=[CH:11][C:9]=3[CH:10]=2)([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:17][C:18]=1[CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57810593HCID 57810593, compound

Product 1

HCID 57810567HCID 57810567, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-{4-[1-ethyl-1-(6-hydroxy-benzofuran-2-yl)-propyl]-2-methyl-phenoxy}-3,3-dimethyl-butan-2-one (116 mg, 0.407 mmol) and Et3N (0.20 mL) in CH2Cl2 (5.0 mL) at 0° C. is added methanesulfonic chloride (70 mg, 0.610 mmol). The resulting mixture is stirred for 30 min and quenched with MeOH (1.0 mL). The mixture is purified on column chromatography (25% EtOAc/Hex) to afford the title compound (185 mg, 93%).

Workup

  1. customquenched with MeOH (1.0 mL)
  2. customThe mixture is purified on column chromatography (25% EtOAc/Hex)

Sources & evidence

ORD record
ord-bd1a302941d34f6388c0b1d1c2c8b24b
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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