Water → HCID 53815124, compound

HRID 2309295Notes

Reaction equation

HRID 2309295 reaction equation
[H-].[Na+].C(=[C:6]([CH:8]([CH2:10][OH:11])[OH:9])[OH:7])(C)C.C1(C)C=CC(S(O[CH2:22][CH2:23][CH:24]([CH3:41])[CH2:25][CH2:26][CH2:27][C@H:28]([CH3:40])[CH2:29][CH2:30][CH2:31][C@H:32]([CH3:39])[CH2:33][CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])(=O)=O)=CC=1.O.[CH3:44][CH2:45][CH2:46]CC>CN(C)C=O>[CH3:44][C:45]1([CH3:46])[O:9][CH:8]([CH2:6][O:7][CH2:22][CH2:23][CH:24]([CH3:41])[CH2:25][CH2:26][CH2:27][C@H:28]([CH3:40])[CH2:29][CH2:30][CH2:31][C@H:32]([CH3:39])[CH2:33][CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[CH2:10][O:11]1

Participants

7

Reactant 5

HCID 962WaterHCID 8003PentaneHCID 24758Sodium hydrideHCID 9920395IsopropylideneglycerolHCID 54298160HCID 54298160, compound

Product 1

HCID 53815124HCID 53815124, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

5.25 g (175 mmol) of sodium hydride (80%) were washed twice with 10 ml of pentane. Thereafter, 400 ml of dimethylformamide and 120 mmol of isopropylideneglycerol were added. The reaction mixture was stirred at 60° C. for 1 hour. After cooling to room temperature 100 mmol of (3RS,7R,11R)-3,7,11,15-tetramethylhexadecyl p-toluenesulphonate in 100 ml of dimethylformamide were added. The reaction mixture was stirred at 60° C. for 2 hours. After the addition of a small amount of water the majority of the solvent was removed at 65° C. The residue was suspended in toluene, filtered and freed from solvent. After chromatography of the crude product on silica gel there was obtained (RS)-2,2-dimethyl-4-[[[(3RS,7R,11R)-3,7,11,15-tetramethylhexadecyl]oxy]methyl]-1,3-dioxolane.

Workup

  1. additionwere added
  2. stirringThe reaction mixture was stirred at 60° C. for 2 hours
  3. customwas removed at 65° C
  4. filtrationfiltered

Sources & evidence

ORD record
ord-9e3388819a8749c2995118d98b0398d5
Source dataset
uspto-grants-1987_09
Patent number
US04694084

Reaction notes

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