4-Methylmorpholine → 3-Phenyloxycarbonyloxymethyl-3-methyloxetane

HRID 265849

Reaction equation

[O:1]([C:8](Cl)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:11][CH2:12][C:13]1([CH3:17])[CH2:16][O:15][CH2:14]1.CN1CCOCC1>C(Cl)Cl>[C:2]1([O:1][C:8]([O:11][CH2:12][C:13]2([CH3:17])[CH2:16][O:15][CH2:14]2)=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 0.552 mL (4.42 mmol) sample of phenoxycarbonylchloride in 2 mL of methylene chloride was added to a solution of 376 mg (3.68 mmol) of 3-hydroxymethyl-3-methyloxetane and 60.7 mL (5.52 mmol) of 4-methylmorpholine in 2 mL of methylene chloride cooled in an ice bath. The mixture was stirred at 0° C. for 3.5 hours. The mixture was diluted with methylene chloride, which was washed with water, dried and concentrated. The crude product was chromatographed on silica gel, eluting with 20% ethyl acetate in hexane. The solvent was removed and the product dried to afford 0.582 g of the title compound, which was taken directly to the next step.

Workup

temperaturecooled in an ice bath
washwas washed with water
customdried
concentrationconcentrated
customThe crude product was chromatographed on silica gel
washeluting with 20% ethyl acetate in hexane
customThe solvent was removed
customthe product dried

Sources & evidence

ORD record: ord-f63ada5e575749e9ae76a5592fd48d78
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05648497

Linked notes

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