Dimethyl Sulfoxide → 79091-88-6

Temperatur

-78 °C

At −78° C., oxalyl Chloride (9.2 mL, 106.5 mmol) was solved in dichloromethane (250 mL) and (15.5 mL, 218 mmol) of dimethylsulfoxide in 20 mL of dichloromethane was added. After 15 minutes of stirring at −78° C., Trans-2-Hydroxymethyl-cyclobutanecarboxylic acid methyl ester (14 g, 95.17 mmol) was added in 78 mL of dichloromethane and 10 minutes later triethylamine (67 mL, 479 mmol) was added and the mixture was stirred for 2 h at −78° C. 150 mL of dichloromethane added and 200 mL of water were added and the aqueous phase was extracted with 200 mL of dichlormethane and the combined organic phases were purified with column chromatography on silica using n-heptane/AcOEt (4+1) to yield 11.1 g, (78 mmol, 82% yield) of the title compound as a colourless liquid. MS (m/e): 165.2 (M+Na+)

1. customAt −78° C.
2. additionwas added
3. stirringthe mixture was stirred for 2 h at −78° C
4. extractionthe aqueous phase was extracted with 200 mL of dichlormethane
5. customthe combined organic phases were purified with column chromatography on silica

ORD-Eintrag

ord-da0f155408bd4a708e99ebdb4e788b64

Quelldatensatz

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08039490B2