4-Toluenesulfonyl chloride → cis-4-p-Toluene-sulphonyloxymethyl-5-benzyloxymethyl cyclohex-1-ene

HRID 2166422Notes

Reaction equation

HRID 2166422 reaction equation
[OH:1][CH2:2][C@H:3]1[C@@H:8]([CH2:9][O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH:6]=[CH:5][CH2:4]1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>N1C=CC=CC=1>[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24]([O:1][CH2:2][C@H:3]2[C@@H:8]([CH2:9][O:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:7][CH:6]=[CH:5][CH2:4]2)(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 67946542{(1R,6S)-6-[(Benzyloxy)methyl]cyclohex-3-en-1-yl}methanol

Product 1

HCID 86740865cis-4-p-Toluene-sulphonyloxymethyl-5-benzyloxymethyl cyclohex-1-eneYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The alcohol/benzyl ether (2) (10 g) in 20 ml of dry pyridine is added slowly at 0° C. to p-toluenesulphonyl chloride (10.4 g) in pyridine (60 ml). The mixture is kept overnight at room temperature and is then quenched by pouring over crushed ice with vigorous shaking. The product is extracted with ether, washed consecutively with water, 0.1M sodium carbonate and brine, dried (MgSO4), and concentrated in vacuo at room temperature. The crude product is purified on a silica gel column, eluting with benzene-ethyl acetate (95%:5% v/v) to give the title compound (14 g, 90%). The i.r. spectrum shows the absence of a hydroxyl group.

Workup

  1. customis then quenched
  2. additionby pouring
  3. customover crushed ice with vigorous shaking
  4. extractionThe product is extracted with ether
  5. washwashed consecutively with water, 0.1M sodium carbonate and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo at room temperature
  8. customThe crude product is purified on a silica gel column
  9. washeluting with benzene-ethyl acetate (95%

Sources & evidence

ORD record
ord-b6941abd59bc4c82a974ada3070a56c5
Source dataset
uspto-grants-1990_07
Patent number
US04945106

Reaction notes

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