Tetrahydrofuran → HCID 18475011, compound

HRID 2227888Notes

Reaction equation

HRID 2227888 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1C[O:34]CC1>>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([OH:34])[C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 3251421Potassium bis(trimethylsilyl)amideHCID 11208638HCID 11208638, compound

Product 1

HCID 18475011HCID 18475011, compoundYield 38%

Procedure

To a solution of methyl 3-(4-tert-butyldimethylsilyloxyphenyl)propionate (5 g, 16.98 mmol) in THF (50 ml) at −78° C. was added dropwise potassium bis(trimethylsilyl)amide (0.5M in toluene, 34 ml, 17 mmol). The mixture was stirred at this temperature for 0.5 hours and treated with dropwise addition of a solution of trans-2-phenylsulfonyl-3-phenyloxaziridine (5.3 g, 20.38 mmol) in THF (30 ml). The mixture was stirred at −78° C. for 1 hour, quenched with aqueous ammonium chloride, warmed to room temperature and diluted with ethyl acetate. The organic phase was washed with aqueous ammonium chloride, brine, dried over sodium sulfate and concentrated in vacuo. Bulb-to-bulb distillation gave the title material (2 g, 38%) as a colorless oil (b.p. 115° C./0.025 mm Hg) which solidified upon standing.

Workup

  1. stirringThe mixture was stirred at −78° C. for 1 hour
  2. customquenched with aqueous ammonium chloride
  3. additiondiluted with ethyl acetate
  4. washThe organic phase was washed with aqueous ammonium chloride, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. distillationdistillation

Sources & evidence

ORD record
ord-c4c038d0fa1d49eea2f098529e4853ec
Source dataset
uspto-grants-2002_07
Patent number
US06414179B1

Reaction notes

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