Cornforth reagent → HCID 66617615, compound

HRID 222190Notes

Reaction equation

HRID 222190 reaction equation
[Si:1]([O:18][CH2:19][C@H:20]1[C@@H:24]([OH:25])[CH:23]=[CH:22][CH2:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[Si:1]([O:18][CH2:19][C@H:20]1[C:24](=[O:25])[CH:23]=[CH:22][CH2:21]1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 58944594HCID 58944594, compound

Product 1

HCID 66617615HCID 66617615, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(1S,5S)-5-({[tert-Butyl(diphenyl)silyl]oxy}methyl)cyclopent-2-en-1-ol (460. mg, 1.30 mmol) was dissolved in DCM (15.0 mL) and pyridinium dichromate (1.47 g, 3.91 mmol) was added. The mixture was stirred at rt overnight, at which point LC/MS indicated complete conversion. The mixture was diluted with DCM (15.0 mL), filtered and concentrated in vacuo. Silica gel chromatography eluting with 0 to 50% EtOAc in hexanes afforded the title compound (400. mg, 79%). LC/MS: Rt=2.42 min, ES+ 351 (AA standard).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. washSilica gel chromatography eluting with 0 to 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-909b51d714f04a4f8c55a6f55d9d9f58
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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