2-Phenylethanol → HCID 23028861, compound

HRID 748831Notes

Reaction equation

HRID 748831 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:20]1([CH2:26][CH2:27]O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[CH2:27][CH2:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 60542-PhenylethanolHCID 4622928CyanomethylenetributylphosphoraneHCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

Product 1

HCID 23028861HCID 23028861, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent2×

Procedure

Under an argon atmosphere, the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (100 mg, 0.330 mmol) obtained in Example 5, and 2-phenylethyl alcohol (79.2 μl, 0.661 mmol) were dissolved in toluene (3 ml), followed by the addition of cyanomethylenetri-n-butylphosphorane (159 μl, 0.661 mmol). The resulting mixture was heated under reflux for 13 hours under an argon atmosphere. The reaction mixture was then concentrated. The residue thus obtained was subjected to flash chromatography on a silica gel column and the fraction obtained from the hexane:ethyl acetate=93:7 eluate was concentrated. The solid thus obtained was washed with hexane, whereby the title compound (100 mg, 0.246 mmol, 74%) was obtained as a white powder.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 13 hours under an argon atmosphere
  3. concentrationThe reaction mixture was then concentrated
  4. customThe residue thus obtained
  5. concentrationethyl acetate=93:7 eluate was concentrated
  6. customThe solid thus obtained

Sources & evidence

ORD record
ord-27a65d233c014886af70ef9036f06014
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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