Water → HCID 6991727, compound

HRID 2413200Notes

Reaction equation

HRID 2413200 reaction equation
[CH3:1][C:2]1([CH3:11])[O:6][C@H:5]([CH2:7][OH:8])[C@@H:4]([CH2:9][OH:10])[O:3]1.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C1COCC1>[C:15]1([CH2:14][O:8][CH2:7][C@@H:5]2[C@@H:4]([CH2:9][O:10][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:3][C:2]([CH3:11])([CH3:1])[O:6]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 78524473346-74-4

Product 1

HCID 6991727HCID 6991727, compoundYield 120.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (4R-trans)-(-)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol (51 g) in THF (400 ml) was added dropwise to a stirred suspension of sodium hydride (17.5 g of 80% in oil) in THF (200 ml). After 0.75 h, benzyl bromide (116.3 g) was added dropwise and the resulting mixture was stirred for 18 h, and was then heated at reflux for 2 h. After stirring for a further 20 h at 20°, the mixture was cooled in ice, water (10 ml) was added and the mixture was evaporated to dryness. The residue was extracted with ER, and the organic solution was dried and the solvent was evaporated giving a crude product (130 g) which was used without further purification.

Workup

  1. temperaturewas then heated
  2. temperatureat reflux for 2 h
  3. stirringAfter stirring for a further 20 h at 20°
  4. temperaturethe mixture was cooled in ice
  5. customthe mixture was evaporated to dryness
  6. extractionThe residue was extracted with ER
  7. customthe organic solution was dried
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f58bc6b713b54d53ac066533d4079a27
Source dataset
uspto-grants-1985_01
Patent number
US04496579

Reaction notes

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