Water → HCID 523368, compound

HRID 612542Notes

Reaction equation

HRID 612542 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][O:5][C:3]1=[O:4].[CH3:8][Si:9](Cl)([CH3:11])[CH3:10].C(N(CC)CC)C.O>C1COCC1.CCOCC>[CH3:8][Si:9]([CH3:11])([CH3:10])[O:1][CH:2]1[CH2:7][CH2:6][O:5][C:3]1=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 545831alpha-Hydroxy-gamma-butyrolactone

Product 1

HCID 523368HCID 523368, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10.0 g (98 mmol) of α-hydroxy-γ-butyrolactone in 100 mL of anhydrous THF under argon was cooled to 0-5° C. with magnetic stirring. Addition of 14 mL (110 mmol) of trimethylsilyl chloride and 16 mL (115 mmol) of triethylamine immediately produced a white precipitate. The suspension was warmed to room temperature and stirred for 4 hours. The suspension was poured into a separatory funnel containing 100 mL of H2O and 500 mL of ether. The organic layer was washed with 50 mL of H2O, 50 mL of brine, dried (MgSO4) and concentrated. Purification (Kugelrohr distillation) provided 14.7 g (90% yield) of α-trimethylsilyloxy-γ-butyrolactone bp 80-100° C. (8 mm Hg).

Workup

  1. customimmediately produced a white precipitate
  2. additionThe suspension was poured into a separatory funnel
  3. washThe organic layer was washed with 50 mL of H2O, 50 mL of brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. distillationPurification (Kugelrohr distillation)

Sources & evidence

ORD record
ord-a2fccfdcbdaa4cabaebb340afc3447a1
Source dataset
uspto-grants-1999_12
Patent number
US06005000

Reaction notes

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