Potassium Bromide → HCID 23245525, compound

HRID 382994Notes

Reaction equation

HRID 382994 reaction equation
[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][C@H:7]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@@H:9]([O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[K+].[Br-].C([O-])(O)=O.[Na+].[O-]Cl.[Na+]>ClCCl.O>[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][C@@H:7]1[CH2:12][C:11](=[O:13])[CH2:10][C@@H:9]([O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 23665760Sodium HypochloriteHCID 69853038HCID 69853038, compound

Product 1

HCID 23245525HCID 23245525, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 27.50 g of (1R,3S,5R)-2,2-dimethyl-propionic acid 3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-cyclohexyl ester in 250 ml of dichloromethane was subsequently added at 0° a solution of 0.713 g of KBr and 2.656 g of NaHCO3 in 250 ml of water and 200 mg of 2,2,6,6-tetramethyl-piperidine-1-oxyl, radical. The stirred mixture was treated at 0° with 61.9 g of NaOCl (11.0%) over 1 h after which time t.l.c. showed completion of the reaction. The layers were separated, the organic layer was washed with 15% aqueous NaCl, dried over MgSO4 and evaporated to give 27.24 g of the pure (t.l.c.) title compound as a yellow oil. IR (neat): 1728s (C═O). MS (EI): 271/5 (M-tert-butyl).

Workup

  1. customcompletion of the reaction
  2. customThe layers were separated
  3. washthe organic layer was washed with 15% aqueous NaCl
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-51fcebc52bbf4b598c57f4591957aafe
Source dataset
uspto-grants-2001_10
Patent number
US06310262B1

Reaction notes

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