Dimethyl Sulfoxide → (+/-)-7-(4-Fluorophenoxy)-6-(2-methoxyethoxymethoxy)-heptan-1-al

HRID 413564Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[CH:33]=[CH:32][C:15]([O:16][CH2:17][CH:18]([O:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])=[CH:14][CH:13]=1>C(Cl)Cl>[F:11][C:12]1[CH:13]=[CH:14][C:15]([O:16][CH2:17][CH:18]([O:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])[CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[O:24])=[CH:32][CH:33]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Oxalyl chloride (2.9 ml, 33.6 mmol) is added to 25 ml of methylene chloride and cooled to −78° C. Dry dimethyl sulfoxide (4.7 ml, 67.2 mmol) is then added and the reaction is stirred at −78° C. After 45 minutes, (±)-7-(4-fluorophenoxy)-6-(2-methoxyethoxymethoxy)-heptan-1-ol 44 (3.7 g, 11.2 mmol) dissolved in CH2Cl2 is added and the reaction is stirred at −78° C. After 1 hour, the reaction is quenched with 15.7 ml of triethylamine and diluted with CH2Cl2. The reaction mixture is then washed with water, brine dried (Na2SO4) and concentrated. The crude product is purified on silica gel (ethyl acetate:hexane 1:9) to give (±)-7-(4-fluorophenoxy)-6-(2-methoxyethoxymethoxy)-heptan-1-al 45, 3.3 g, 89%.

Workup

additionis added
stirringthe reaction is stirred at −78° C
waitAfter 1 hour
customthe reaction is quenched with 15.7 ml of triethylamine
additiondiluted with CH2Cl2
washThe reaction mixture is then washed with water, brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe crude product is purified on silica gel (ethyl acetate:hexane 1:9)

Sources & evidence

ORD record: ord-344ae656ea1c4a179374800e162cde16
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06566538B1

Reaction notes

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