Methanesulfonyl chloride → HCID 57508922, compound

HRID 1665964Notes

Reaction equation

HRID 1665964 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][CH2:15][C:16]([C:18]2[S:19][C:20]([CH3:29])=[C:21]3[CH2:26][C:25]([CH3:28])([CH3:27])[CH2:24][CH2:23][C:22]=23)=[O:17])[CH:5]=[C:6]([O:12][CH3:13])[C:7]=1[O:8][CH2:9][CH2:10][OH:11].CCN(C(C)C)C(C)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][CH2:15][C:16](=[O:17])[C:18]2[S:19][C:20]([CH3:29])=[C:21]3[CH2:26][C:25]([CH3:27])([CH3:28])[CH2:24][CH2:23][C:22]=23)[CH:5]=[C:6]([O:12][CH3:13])[C:7]=1[O:8][CH2:9][CH2:10][O:11][S:40]([CH3:39])(=[O:42])=[O:41]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 57437436HCID 57437436, compound

Product 1

HCID 57508922HCID 57508922, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-[3-chloro-4-(2-hydroxyethoxy)-5-methoxy-phenyl]-1-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propan-1-one (160 mg, 0.40 mmol) in DCM (10 mL) and DIPEA (0.11 mL, 0.64 mmol) is added methane sulfonylchloride (0.04 mL, 0.48 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-chloro-6-methoxy-4-[3-oxo-3-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propyl]-phenoxy}-ethyl ester (183 mg) as a yellow oil; LC-MS: tR=1.15 min, [M+1]+=515.15.

Workup

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

Sources & evidence

ORD record
ord-f12e3cb5edfc4e95bcb357dfc52c7f13
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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