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 1080509Notes

Reaction equation

HRID 1080509 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-5a240d8574bc4b2aa33e0733f83fdb1c
Source dataset
uspto-grants-1996_12
Patent number
US05580999

Reaction notes

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