Triphenylphosphine → 6-[(3,3-Difluorocyclobutyl)methoxy]-2,3-dihydro-1H-inden-1-one

HRID 1468069노트

반응식

HRID 1468069 반응식
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[F:12][C:13]1([F:19])[CH2:16][CH:15]([CH2:17]O)[CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[F:12][C:13]1([F:19])[CH2:16][CH:15]([CH2:17][O:1][C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][CH2:7][C:8]3=[O:11])=[CH:4][CH:3]=2)[CH2:14]1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 70206596-Hydroxy-1-indanoneHCID 45480377(3,3-Difluorocyclobutyl)methanol

생성물 1

HCID 867067186-[(3,3-Difluorocyclobutyl)methoxy]-2,3-dihydro-1H-inden-1-one수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 6-hydroxy-2,3-dihydro-1H-inden-1-one (3.6 g, 24.3 mmol) in THF (60 mL) were (3,3-difluorocyclobutyl)methanol (2.97 g, 24.3 mmol) and triphenylphosphine (9.56 g, 36.45 mmol) added. Diisopropyl azodicarboxylate (7.18 mL, 36.5 mmol) was added dropwise. The reaction mixture was stirred at r.t. overnight. The material was purified by flash column chromatography using a gradient of 0-100% EtOAc in heptane, providing 3.67 g (60% yield) of the title compound. 1H NMR (500 MHz, DMSO-d6) ppm 2.30 (br. s., 1H) 2.42-2.52 (m, 6H) 2.54-2.62 (m, 1H) 2.63-2.66 (m, 2H) 2.67-2.76 (m, 2H) 2.98-3.04 (m, 2H) 4.08 (d, 2H) 7.10 (d, 1H) 7.26 (dd, 1H) 7.48 (d, 1H); MS (ES+) m/z 253 [M+H]+.

후처리

  1. additionadded
  2. customThe material was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-acb985c483774953a2b2e29df3e02d41
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000185B2

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