tert-Butanol → HCID 86744755, compound

HRID 1085994Notes

Reaction equation

HRID 1085994 reaction equation
[CH2:1]([S:4][C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:2]=[CH2:3].[C:24](O)([CH3:27])([CH3:26])C.C[C:30]([CH3:33])([O-])[CH3:31]>O1CCCC1>[CH:19](/[C:12]1([CH:13]=[CH:14][CH:15]=[CH:16][CH2:17]1)[C:5]([S:4][C:1]([C:26]1[CH:24]=[CH:27][CH:12]=[CH:5][CH:6]=1)([C:31]1[CH:30]=[CH:33][CH:3]=[CH:2][CH:1]=1)[C:2]1(/[CH:13]=[CH:14]/[CH3:15])[CH:7]=[CH:8][CH:9]=[CH:10][CH2:3]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH:18]\[CH3:23]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 637326Allyl tritylsulfideHCID 45749132-Methylpropan-2-olate

Product 1

HCID 86744755HCID 86744755, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Then, 12.64 g of allyl tritylsulfide was dissolved in a solvent mixture consisting of 130 ml of t-butanol and 70 ml of tetrahydrofuran, and 9.0 g of pottasium tert. -butoxide was added to the resulting solution at room temperature with stirring, and the mixture was further stirred for 15 hours. The solvents were removed from the reaction mixture at a temperature of below 40° C. by distillation under reduced pressure, and then 200 ml of water and 400 ml of benzene were added to the residue to extract. The benzene layer was washed with water and dried over anhydrous magnesium sulfate. Then, the solvent was removed therefrom by distillation under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with n-hexane, whereby 5.0 g of trans 1-propenyl tritylsulfide (melting point: 105°-106° C.) was obtained as colorless crystal.

Workup

  1. additionwas added to the resulting solution at room temperature
  2. stirringthe mixture was further stirred for 15 hours
  3. customThe solvents were removed from the reaction mixture at a temperature of below 40° C. by distillation under reduced pressure
  4. addition200 ml of water and 400 ml of benzene were added to the residue
  5. extractionto extract
  6. washThe benzene layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThen, the solvent was removed
  9. distillationby distillation under reduced pressure
  10. washeluted with n-hexane

Sources & evidence

ORD record
ord-8031893125634a11bc95f4b43ccce2be
Source dataset
uspto-grants-1991_04
Patent number
US05011975

Reaction notes

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