Water → HCID 22033293, compound

HRID 1792327Notes

Reaction equation

HRID 1792327 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[S:14][CH2:13][C:12]1([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[CH3:23].[CH3:31][S:32](Cl)(=[O:34])=[O:33].C(N(CC)CC)C.O>ClCCl.C(OCC)(=O)C.CCCCCC>[F:30][C:27]1[CH:26]=[CH:25][C:24]([C:12]2([CH3:23])[CH:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:1][S:32]([CH3:31])(=[O:34])=[O:33])[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[S:14][CH2:13]2)=[CH:29][CH:28]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22033044HCID 22033044, compound

Product 1

HCID 22033293HCID 22033293, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(9-Hydroxynonyl)-3-(4-fluorophenyl)-7-methoxy-3-methylthiochroman (0.41 g, 0.95 mmol) was dissolved in dichloromethane (50 ml), methanesulfonyl chloride (0.44 g) and triethylamine (0.41 g) were added thereto, and the mixture was stirred at room temperature for 1 hour. After the reaction was completed, water was poured thereto, and the mixture was extracted with chloroform (50 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a crude product. This crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=3:1) to give 3-(4-fluorophenyl)-4-(9-methanesulfonyloxynonyl)-7-methoxy-3-methylthiochroman (a mixture of (3RS,4RS) and (3RS, 4SR), (3RS,4RS)/(3RS,4SR)=about 6/1) (480 mg, yield 99%).

Workup

  1. extractionthe mixture was extracted with chloroform (50 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a crude product
  5. customThis crude product thus obtained

Sources & evidence

ORD record
ord-cf840f5d644249b5ad13bf3fb026acef
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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