Triphenylphosphine → 2-[2,2-Dimethyl-4-(4-methylphenyl)oxan-4-yl]acetaldehyde

HRID 626477Notes

Reaction equation

HRID 626477 reaction equation
[O:1]=[O+][O-].[CH3:4][C:5]1([CH3:21])[CH2:10][C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)([CH2:11][CH:12]=C)[CH2:8][CH2:7][O:6]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH3:4][C:5]1([CH3:21])[CH2:10][C:9]([CH2:11][CH:12]=[O:1])([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH2:8][CH2:7][O:6]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823OzoneHCID 683142852,2-Dimethyl-4-(4-methylphenyl)-4-(prop-2-en-1-yl)oxane

Product 1

HCID 866714262-[2,2-Dimethyl-4-(4-methylphenyl)oxan-4-yl]acetaldehydeYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

O3 gas was passed through a solution of 2,2-dimethyl-4-(4-methylphenyl)-4-(prop-2-en-1-yl)oxane (1.21 g, 5 mmol) in CH2Cl2 (50 ml) at −78° C. until the solution turned light blue (about 5 min). After additional 5 minutes, the reaction mix was purged with oxygen gas for 15 min before adding triphenylphosphine (2.62 g, 10 mmol). The reaction was stirred at rt for 4 h and concentrated. Purified by normal phase SiO2 chromatography (10 to 60% EtOAc/hexanes) to give 2-[2,2-dimethyl-4-(4-methylphenyl)oxan-4-yl]acetaldehyde as a colorless oil (641 mg, 52%).

Workup

  1. custom(about 5 min)
  2. additionthe reaction mix
  3. customwas purged with oxygen gas for 15 min
  4. concentrationconcentrated
  5. customPurified by normal phase SiO2 chromatography (10 to 60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-72802c3a38924ef59e6140b1a7563ecf
Source dataset
uspto-grants-2016_04
Patent number
US09309234B2

Reaction notes

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