N-bromobutanimide → 7-Bromo-6-hydroxy-1-heptanol

반응식

[CH2:1]([OH:8])[CH2:2][CH2:3][CH2:4]CC=C.[Br:9]N1C(=O)CCC1=O.[C:17]([OH:21])(C)([CH3:19])[CH3:18].O>>[Br:9][CH2:18][CH:17]([OH:21])[CH2:19][CH2:4][CH2:3][CH2:2][CH2:1][OH:8]

참가 물질

반응물 3

HCID 67184N-bromobutanimide3회

HCID 543123Hept-6-en-1-ol

HCID 714019492-Methylpropan-2-ol--water (1/1)

생성물 1

HCID 133660747-Bromo-6-hydroxy-1-heptanol

실험 절차

To a solution of 3 (500 mg, 4.38 mmol) in t-butanol-water (24 mL-4 mL) in the dark was added N-bromosuccinimide (NBS) (858 mg, 4.82 mmol) in small portions. Additional NBS (312 mg) was added after 4 hours and 16 hours later another 400 mg of NBS was added. The reaction mixture was stirred for 68 hours. After removal of t-butanol in vacuo, the residue was diluted with ether, washed with saturated sodium thiosulfite solution, saturated sodium chloride solution, and dried over magnesium sulfate. The crude product was purified by HPLC to give 123 mg of 7-bromo-6-hydroxy-1-heptanol (4).

후처리

additionwas added
customAfter removal of t-butanol in vacuo
additionthe residue was diluted with ether
washwashed with saturated sodium thiosulfite solution, saturated sodium chloride solution
dry with materialdried over magnesium sulfate
customThe crude product was purified by HPLC

출처 및 근거

ORD 기록: ord-ba6d27e779a340eda1b70c0430433cb5
출처 데이터셋: uspto-grants-1984_06
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US04456613

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