Triphenylphosphine → (S)-3,5-di-(tert-butyldimethylsilyloxy)-pentan-2-one

HRID 1740484Notes

Reaction equation

HRID 1740484 reaction equation
O=[O+][O-].[Si:4]([O:11][CH2:12][CH2:13][C@H:14]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C:15](C)=[CH2:16])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCCCC.CC[O:52]CC>O=O.ClCCl>[Si:19]([O:18][C@@H:14]([CH2:13][CH2:12][O:11][Si:4]([C:7]([CH3:8])([CH3:9])[CH3:10])([CH3:5])[CH3:6])[C:15](=[O:52])[CH3:16])([C:22]([CH3:23])([CH3:24])[CH3:25])([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 24823OzoneHCID 11336893(S)-1,3-Di-[(tert-butyldimethylsilyloxy)]-4-methyl-4-pentene2×HCID 21877078Diethylether pentane

Product 1

HCID 11782967(S)-3,5-di-(tert-butyldimethylsilyloxy)-pentan-2-oneYield 70%

Reagents, catalysts & solvents 2

HCID 977OxygenSolventHCID 6344DichloromethaneSolvent

Procedure

Ozone in O2 is directed at -78° C. through a solution of 1.610 g (4.67 mmol) of 11 in 200 ml of absolute dichloromethane (dry ice/acetone-cold bath). When starting compound 11 can no longer be detected by thin-layer chromatography in the solution, 3.89 g (14.83 mmol) of triphenylphosphine is added, and the cold bath is removed. The reaction batch is allowed to come slowly to room temperature, and the solvent is distilled off in a vacuum. Flash chromatography of the residue by a silica gel column with pentane/Et2O (50:1) yields 1.135 g (3.27 mmol, 70%) of 12.

Workup

  1. additionis added
  2. customthe cold bath is removed
  3. customto come slowly to room temperature
  4. distillationthe solvent is distilled off in a vacuum

Sources & evidence

ORD record
ord-3568f54026754d0baedf6ad03d1fd21b
Source dataset
uspto-grants-1999_10
Patent number
US05969145

Reaction notes

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