p-Toluenesulfonic acid → 2-[(4S)-2,2-diethyl-1,3-dioxolan-4-yl]ethanol

HRID 1961522Notes

Reaction equation

HRID 1961522 reaction equation
[CH2:1]([OH:7])[C@@H:2]([OH:6])[CH2:3][CH2:4][OH:5].[CH3:8][CH2:9][C:10](=O)[CH2:11][CH3:12].C1(C)C=CC(S(O)(=O)=O)=CC=1>CCN(CC)CC>[CH2:9]([C:10]1([CH2:11][CH3:12])[O:6][C@@H:2]([CH2:3][CH2:4][OH:5])[CH2:1][O:7]1)[CH3:8]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7288Ethyl ketoneHCID 6409971,2,4-Butanetriol, (2S)-

Product 1

HCID 109759852-[(4S)-2,2-diethyl-1,3-dioxolan-4-yl]ethanol

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
53 °C

Procedure

To a solution of (S)-1,2,4-butanetriol intermediate 67a (6.76 g, 63.68 mmol) in freshly distilled pentan-3-one (320 mL) was added p-toluenesulfonic acid (p-TSA) (6.06 g, 31.84 mmol). The reaction mixture was stirred at 53° C. for 16 hours, then Et3N (10 mL) was added and the reaction mixture stirred at ambient temperature for 10 minutes. The reaction mixture was concentrated under reduced pressure. Gradient flash chromatography (CH2Cl2/MeOH, 100:0 to 97:3 to 95:5) afforded the protected alcohol intermediate 67b (9.84 g, 89%) as a colorless oil.

Workup

  1. stirringthe reaction mixture stirred at ambient temperature for 10 minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6b61ec3f64364d59a72f8742963b81da
Source dataset
uspto-grants-2013_04
Patent number
US08415347B2

Reaction notes

Loading…