Methanesulfonyl chloride → HCID 57508920, compound

HRID 1665962Notes

Reaction equation

HRID 1665962 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH2:12][CH2:13][C:14]([C:16]2[S:17][C:18]([CH3:27])=[C:19]3[CH2:24][C:23]([CH3:26])([CH3:25])[CH2:22][CH2:21][C:20]=23)=[O:15])=[CH:7][C:6]=1[CH3:28].CCN(C(C)C)C(C)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(Cl)Cl>[CH3:11][C:10]1[CH:9]=[C:8]([CH2:12][CH2:13][C:14](=[O:15])[C:16]2[S:17][C:18]([CH3:27])=[C:19]3[CH2:24][C:23]([CH3:25])([CH3:26])[CH2:22][CH2:21][C:20]=23)[CH:7]=[C:6]([CH3:28])[C:5]=1[O:4][CH2:3][CH2:2][O:1][S:39]([CH3:38])(=[O:41])=[O:40]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 11852049HCID 11852049, compound

Product 1

HCID 57508920HCID 57508920, compoundYield 106.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-1-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propan-1-one (130 mg, 0.325 mmol) in DCM (10 mL) and DIPEA (0.09 mL, 0.52 mmol) is added methane sulfonylchloride (0.03 mL, 0.39 mmol) at 0° C. The reaction mixture is stirred at 0° C. for 30 min. The reaction mixture is diluted with DCM, washed with 0.1 N aq. NaOH followed by 10% aq. citric acid solution, dried over MgSO4 and evaporated to give methanesulfonic acid 2-{2,6-dimethyl-4-[3-oxo-3-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propyl]-phenoxy}-ethyl ester (165 mg) as a yellow oil; LC-MS: tR=1.17 min, [M+1]+=479.26.

Workup

  1. washwashed with 0.1 N aq. NaOH
  2. dry with materialdried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-80032170218f47b795faade539b68dd1
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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