Dimethyl Sulfoxide → (2R,3S,4S,5Z)-3-[(4-methoxyphenyl)methoxy]-2,4-dimethyl-5,7-octadienal

HRID 857964Notes

Reaction equation

HRID 857964 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][C@@H:11]([C@@H:16]([CH3:21])/[CH:17]=[CH:18]\[CH:19]=[CH2:20])[C@@H:12]([CH3:15])[CH2:13][OH:14])=[CH:5][CH:4]=1.CS(C)=O.CCN(CC)CC.C(Cl)Cl>CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][O:10][C@@H:11]([C@@H:16]([CH3:21])/[CH:17]=[CH:18]\[CH:19]=[CH2:20])[C@@H:12]([CH3:15])[CH:13]=[O:14])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 6344DichloromethaneHCID 8471TriethylamineHCID 10684929(2S,3S,4S,5Z)-3-[(4-methoxyphenyl)methoxy]-2,4-dimethyl-5,7-octadien-1-ol

Product 1

HCID 11044422(2R,3S,4S,5Z)-3-[(4-methoxyphenyl)methoxy]-2,4-dimethyl-5,7-octadienalYield 98.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of (2S,3S,4S,5Z)-3-[(4-methoxyphenyl)methoxy]-2,4-dimethyl-5,7-octadien-1-ol (2.0 g, 6.9 mmol), DMSO (2.1 mL), NEt3 (2.79 g, 27.59 mmol) and methylene chloride (20 mL) is cooled to 0° C., and is treated with SO3-Pyr (3.29 g, 20.69 mmol) and DMSO (8 mL) over 10 min. After additional 2 h at 0° C., the mixture is diluted with ether (200 mL), washed with 1 M aqueous NaHSO4 (100 mL), brine (100 mL), and concentrated. Flash chromatography (1% to 10% ethyl acetate in hexane) gives the desired compound (1.95 g, 98.2%) as a colorless oil.

Workup

  1. washwashed with 1 M aqueous NaHSO4 (100 mL), brine (100 mL)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-742fc60055564a629492bfe551a82b0b
Source dataset
uspto-grants-2006_12
Patent number
US07148218B2

Reaction notes

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