beta(R)-benzyloxy-1,4-dioxaspiro[4,5]decane-2(R)-ethanol → alpha(S)-benzyloxy-1,4-dioxaspiro[4,5]decane-2(R)-acetaldehyde

HRID 440108Notes

Reaction equation

HRID 440108 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]([O:19][C@@H:20]([C@H:23]1[CH2:27][O:26][C:25]2([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[O:24]1)[CH2:21][OH:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl.C(OCC)C>[CH2:12]([O:19][C@@H:20]([C@H:23]1[CH2:27][O:26][C:25]2([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[O:24]1)[CH:21]=[O:22])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 53702433beta(R)-benzyloxy-1,4-dioxaspiro[4,5]decane-2(R)-ethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 22856132alpha(S)-benzyloxy-1,4-dioxaspiro[4,5]decane-2(R)-acetaldehydeYield 77.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

15.0 g of pyridinium chlorochromate and 10.0 g of crushed 3A molecular sieves were added to a solution of 5.50 g (0.019 mol) of β(R)-benzyloxy-1,4-dioxaspiro[4,5]decane-2(R)-ethanol in 200 ml of dichloromethane. The mixture was stirred at room temperature for 20 hours, then diluted with 200 ml of diethyl ether and filtered. The filtrate was evaporated to give 4.30 g of α(S)-benzyloxy-1,4-dioxaspiro[4,5]decane-2(R)-acetaldehyde which was used in the next step without further purification.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-7abb0e9c6a7a4d72981bf6e994fab3dc
Source dataset
uspto-grants-1996_05
Patent number
US05516913

Reaction notes

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