Triphenylphosphine → HCID 86611582, compound

HRID 1432098Notes

Reaction equation

HRID 1432098 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]([CH:18]1[CH2:22][CH2:21][C:20](=[O:23])[O:19]1)[CH2:9][CH:10]([CH3:17])[CH2:11][CH2:12][CH:13]=C(C)C)([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=[O:26].[Na+].O=[O+][O-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O=O.CO.C(Cl)Cl>[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]([CH:18]1[CH2:22][CH2:21][C:20](=[O:23])[O:19]1)[CH2:9][CH:10]([CH3:17])[CH2:11][CH2:12][CH:13]=[O:26])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 24823OzoneHCID 516892Sodium BicarbonateHCID 68546501HCID 68546501, compound

Product 1

HCID 86611582HCID 86611582, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 977OxygenSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5.4 g (15.9 mmol) of [(R)-3,7-dimethyl-1-(5-oxo-tetrahydro-furan-2-yl)oct-6-enyl]-carbamic acid tert-butyl ester (preparation of aldehyde in step g of example 6) in a mixture 200 ml DCM and 10 ml MeOH is cooled to −70° C. After addition of 0.63 g (7.5 mmol) NaHCO3 a stream of O3 in O2 is passed through the stirred mixture till a blue color persists. The excess ozone is removed by passing through more oxygen. After addition of 5.0 g (19 mmol) triphenylphosphine the mixture is allowed to warm up at rt and stirred for 4 h. The mixture is filtered and concentrated in vacuo. Chromatography on silica gel (EtOAc/Hexane 1:1) gives the title aldehyde.

Workup

  1. customThe excess ozone is removed
  2. filtrationThe mixture is filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4501203d4e0b44d1a6bfdd162ead02aa
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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