Triethylamine → HCID 57835390, compound

HRID 730993Notes

Reaction equation

HRID 730993 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[S:10][C:9]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:8]=2[CH:7]=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[S:10][C:9]3[CH:11]=[CH:12][C:13]([O:15][S:39]([CH3:38])(=[O:41])=[O:40])=[CH:14][C:8]=3[CH:7]=2)([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:17][C:18]=1[CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57835418HCID 57835418, compound

Product 1

HCID 57835390HCID 57835390, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-{4-[1-ethyl-1-(5-hydroxy-benzo[b]thiophen-2-yl)-propyl]-2-methyl-phenoxy}-3,3-dimethyl-butan-2-one (260 mg, 0.612 mmol) in CH2Cl2 (20 mL) at RT is treated with Et3N (0.40 mL) and methanesulfonyl chloride (140 mg, 1.22 mmol). The mixture is stirred for 30 min and quenched with water (1.0 mL). The organic layer is concentrated and purified using silica gel column chromatography (25% EtOAc/Hex) to afford the title compound (190 mg, 62%). NMR (ppm, CDCl3), δ: 7.67 (1 H, d, J=8.8 Hz), 7.59 (1 H, d, J=2.2 Hz), 7.13 (1 H, dd, J=2.2, 8.8 Hz), 7.11 (1 H, s), 7.01-7.04 (2 H, m), 6.51 (1 H, d, J=8.4 Hz), 4.84 (2 H, s), 3.16 (3 H, s), 2.26 (3 H, s), 2.15 (4 H, q, J=7.5 Hz), 1.26 (9 H, s), 0.74 (6H, t, J=7.5 Hz).

Workup

  1. customquenched with water (1.0 mL)
  2. concentrationThe organic layer is concentrated
  3. custompurified

Sources & evidence

ORD record
ord-fe2e8c109c5a47928b5b0871bba1f4c1
Source dataset
uspto-grants-2009_09
Patent number
US07582775B2

Reaction notes

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