Carbon Dioxide → HCID 178459559, compound

HRID 330617Notes

Reaction equation

HRID 330617 reaction equation
[CH2-:1][C:2]([CH3:4])=[O:3].[CH2:5]([C:7]([OH:14])([CH2:10][CH2:11][CH:12]=C)[CH2:8][OH:9])[CH3:6].C(=O)=[O:16].O=[O+][O-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl.CC(C)=O>[CH2-:1][C:2]([CH3:4])=[O:3].[CH2:5]([C:7]([OH:14])([CH2:8][OH:9])[CH2:10][CH2:11][CH:12]=[O:16])[CH3:6]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 11776TriphenylphosphineHCID 24823OzoneHCID 178447079HCID 178447079, compound2×

Product 1

HCID 178459559HCID 178459559, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2S 2-ethyl-2-hydroxyhex-5-enol acetonide (1.2 g, 6.52 mmol) in dichloromethane (25 mL) was brought to -78° C. (dry ice, acetone) and ozone was bubbled through until the reaction mixture turned a pale blue (approx. 15 min.). The reaction mixture was then flushed with nitrogen for 1 h, triphenylphosphine (850 mg, 3.26 mmole) was added and the mixture was allowed to slowly warm to room temperature. The solvent was removed under reduced pressure and the residue was taken up in hexane, filtered and again concentrated. Flash chromatography on 50 g of silica gel, eluting with 3:2 hexane/ether, gave 0.92 g (76%) of the title aldehyde. TLC Rf 0.39 (silica gel, 3:2 hexane-ether).

Workup

  1. customwas brought to -78° C.
  2. customwas bubbled through until the reaction mixture
  3. customa pale blue (approx. 15 min.)
  4. customThe reaction mixture was then flushed with nitrogen for 1 h
  5. customThe solvent was removed under reduced pressure
  6. filtrationfiltered
  7. concentrationagain concentrated
  8. washFlash chromatography on 50 g of silica gel, eluting with 3:2 hexane/ether

Sources & evidence

ORD record
ord-e980a80277074b739e07e009a241c2cd
Source dataset
uspto-grants-1990_01
Patent number
US04897477

Reaction notes

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