Tetrahydrofuran → 2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethanol

HRID 2215207Notes

Reaction equation

[CH:1]1([C:7]2[O:8][C:9]([CH3:16])=[C:10]([CH2:12][C:13](O)=[O:14])[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1COCC1.B.C1COCC1>CO>[CH:1]1([C:7]2[O:8][C:9]([CH3:16])=[C:10]([CH2:12][CH2:13][OH:14])[N:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 50 °C

Procedure

1.920 g of the above prepared (2-cyclohexyl-5-methyl-oxazol-4-yl)-acetic acid (8.60 mmol) was dissolved in 56 ml of abs. THF and treated at 0° C. with 21.5 ml of 1M BH3THF (2.5 eq.). The reaction mixture was then kept over weekend at ambient temperature. 3.5 ml of MeOH was added and the mixture stirred for 3 h at ambient temperature and for 3 h at 50° C. to liberate the free alcohol. Removing of the solvents i. V., followed by flash chromatography (SiO2, hexane/AcOEt=4/6) yielded finally 1.314 g of the title compound as colorless oil.

Workup

dissolutionwas dissolved in 56 ml of abs
waitThe reaction mixture was then kept over weekend at ambient temperature
customRemoving of the solvents i

Sources & evidence

ORD record: ord-dd2d681717be4f00bd6b834d8c247d5e
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109225B2

Reaction notes

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