Ethyl Acetate → 6-Bromo-3 4-dihydro-4,4-dimethyl-8-vinylspiro[2H-1-benzopyran-2,1'-cyclopropane]

HRID 24111

반응식

HRID 24111 반응식
[CH2:1]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br:21][C:22]1[CH2:23][C:24](=[C:36]=O)[C:25]2[O:32][C:29]3([CH2:31][CH2:30]3)[CH2:28][C:27]([CH3:34])([CH3:33])[C:26]=2[CH:35]=1.C(OCC)(=O)C>CCCCCC>[Br:21][C:22]1[CH:23]=[C:24]([CH:36]=[CH2:1])[C:25]2[O:32][C:29]3([CH2:31][CH2:30]3)[CH2:28][C:27]([CH3:34])([CH3:33])[C:26]=2[CH:35]=1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 137960MethylenetriphenylphosphoraneHCID 181779686-bromo-8-carbonyl-3,4-dihydro-4,4-dimethylspiro [2H-1-benzopyran-2,1'-cyclopropane]2회

생성물 1

HCID 225688556-Bromo-3 4-dihydro-4,4-dimethyl-8-vinylspiro[2H-1-benzopyran-2,1'-cyclopropane]

시약·촉매·용매 1

HCID 8058Hexane용매

실험 절차

Following general procedure N and using A solution of methylidene triphenyl phosphorane [generated from methyl triphenylphosphonium bromide (7 g, 20 mmol) and 1.6M solution of n-butyl lithium in hexanes (11.8 mL, 19 mmol)], 6-bromo-8-carbonyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1′-cyclopropane](Intermediate 40, 2.06 g, 7 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 1-2% ethyl acetate in hexane as the eluent, the title compound was obtained as a clear oil (1.36 g, 66%).

출처 및 근거

ORD 기록
ord-32d9f729b81e4268b027aedee27a797c
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855512B2

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