Triethylamine → HCID 58668690, compound

HRID 2356985Notes

Reaction equation

HRID 2356985 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]([CH2:21][CH2:22][OH:23])[CH2:16][CH2:17][O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]([CH2:21][CH2:22][O:23][S:32]([CH3:31])(=[O:34])=[O:33])[CH2:16][CH2:17][O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68459038HCID 68459038, compound

Product 1

HCID 58668690HCID 58668690, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-[7-(3-Fluoro-benzenesulfonyl)-chroman-4-yl]-ethanol (1.35 g, 4.01 mmol) in CH2Cl2 (40 ml) was cooled to 0° C. Et3N (4.06 g, 40.2 mmol) was added at 0° C. followed by methanesulfonylchloride (0.91 g, 8.00 mmol). The reaction mixture was stirred in an ice bath for 2 hours, then diluted with CH2Cl2, washed with brine, dried with MgSO4, filtered and concentrated to give AN oil residue. The residue was purified with flash chromatography to give methanesulfonic acid 2-[7-(3-fluoro-benzenesulfonyl)-chroman-4-yl]-ethyl ester as a clear oil: 1.35 g; MS: 415.2 (M+H)+, 829.2 (2M+H)+.

Workup

  1. washwashed with brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give AN oil residue
  6. customThe residue was purified with flash chromatography

Sources & evidence

ORD record
ord-8ffc61180c504e75bffe95904e7ca66a
Source dataset
uspto-grants-2010_07
Patent number
US07759389B2

Reaction notes

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