Water → HCID 22841818, compound

HRID 1461400Notes

Reaction equation

HRID 1461400 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][C:10]([CH2:14][CH2:15][CH2:16][CH2:17][O:18]C2CCCCO2)=[C:9]1[CH3:25])(=[O:3])[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>C(O)C>[C:1]([O:4][CH2:5][CH2:6][CH2:7][C@H:8]1[CH2:13][CH2:12][CH2:11][C:10]([CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[C:9]1[CH3:25])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 53907572HCID 53907572, compound

Product 1

HCID 22841818HCID 22841818, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 7.3 g (20.7 mmole) of [R-(R*,S*)]-3-[4-[(tetrahydro-2H-pyran-2yl)oxy]butyl]-2-methyl-2-cyclohexene-1-propanol acetate in 68 ml of absolute ethanol was added 530 mg (2.1 mmole) of pyridinium p-toluenesulfonate and the homogeneous solution heated at 50° C. for 4 hours. The cooled reaction mixture was poured into 280 ml of water and extracted with 3×350 ml of ether. The combined organic extracts were washed with NaHCO3, brine, dried over MgSO4, filtered and concentrated. The crude product was chromatographed on a silica gel column (5:1, hexane/EtOAc) to give 4.3 g (78%) of (R)-3-[3-(acetyloxy)propyl]-2-methyl-1-cyclohexene-1-butanol as an oil.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with 3×350 ml of ether
  3. washThe combined organic extracts were washed with NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was chromatographed on a silica gel column (5:1, hexane/EtOAc)

Sources & evidence

ORD record
ord-472cf22892414c3aac07b7d3727f7bea
Source dataset
uspto-grants-1991_12
Patent number
US05075327

Reaction notes

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