Water → HCID 21273118, compound

HRID 1382706Notes

Reaction equation

HRID 1382706 reaction equation
[CH2:1]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1/[CH:16]=[CH:17]/[CH2:18][CH2:19][CH2:20][CH2:21]O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C(N(S(F)(F)[F:29])CC)C.O>ClCCl>[F:29][CH2:21][CH2:20][CH2:19][CH2:18]/[CH:17]=[CH:16]/[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 21273115HCID 21273115, compound

Product 1

HCID 21273118HCID 21273118, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 8.17 g of -(2-nonylphenyl)-1-trans-hexen-6-ol in 20 ml of dichloromethane is added dropwise over a period of 20 minutes to a mixture, cooled with an ice-bath and stirred under an argon atmosphere, of 4.68 g of diethylaminosulphur trifluoride in 20 ml of dichloromethane. After further stirring at room temperature for 14 hours, water is added, and the organic layer is separated off and washed with saturated sodium bicarbonate solution and water. The crude product remaining after the organic phase has been dried and concentrated by evaporation is purified by flash chromatography on silica gel with petroleum ether. The title compound is obtained in the form of a colourless oil.

Workup

  1. temperaturecooled with an ice-bath
  2. customthe organic layer is separated off
  3. washwashed with saturated sodium bicarbonate solution and water
  4. customhas been dried
  5. concentrationconcentrated by evaporation
  6. customis purified by flash chromatography on silica gel with petroleum ether

Sources & evidence

ORD record
ord-32f2b4a4836b46c59dd2b1c41c23613c
Source dataset
uspto-grants-1989_02
Patent number
US04808572

Reaction notes

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