Cyclopentene → 3,3'-Dicyclopentyl-5,5',6,6',7,7',8,8'-octahydro-2,2'-binapthol

HRID 1790996

반응식

HRID 1790996 반응식
[C:1]1([OH:21])[C:2]([C:11]2[CH:20]=[CH:19][C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[CH:12]=2)=[CH:3][CH:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH2:7][CH2:6]2.[CH:22]1[CH2:26][CH2:25][CH2:24][CH:23]=1>O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W]>[CH:22]1([C:3]2[CH:4]=[C:5]3[C:10]([CH2:9][CH2:8][CH2:7][CH2:6]3)=[C:1]([OH:21])[C:2]=2[C:11]2[C:20]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:19][C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[CH:12]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

참가 물질

4

반응물 2

HCID 8882CyclopenteneHCID 220441995,5',6,6',7,7',8,8'-Octahydro-2,2'-binaphthol

생성물 1

HCID 865882763,3'-Dicyclopentyl-5,5',6,6',7,7',8,8'-octahydro-2,2'-binapthol수율 42%

시약·촉매·용매 1

HCID 45231312-Wolframophosphoric acid촉매

실험 절차

A mixture of 5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binapthol (48 g), phosphotungstic acid (2.4 g) and cyclopentene (58 g) was charged into a Hastelloy reactor. The reactor was heated to 180 C for 40 hours. The mixture was purified by column chromatography (silica gel, eluting with 2% ethyl acetate/hexane) to yield 29.5 g (42%) of 3,3′-dicyclopentyl-5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binapthol, mp 143–152° C. 13C NMR (CDCl3): 22.96, 25.31, 26.68, 29.19, 32.72, 32.75, 39.20, 118.58, 128.14, 129.20, 129.74, 133.91, 149.14 ppm. 1H NMR (CDCl3): 1.60 (m, 10H), 2.0 (d, 4H), 2.65 (t, J=4 Hz, 2H), 3.27 (quintet, J=7 Hz, 1H), 4.55 (s, 1H), 6.92 (s, 1H) ppm.

후처리

  1. additionwas charged into a Hastelloy reactor
  2. temperatureThe reactor was heated to 180 C for 40 hours
  3. customThe mixture was purified by column chromatography (silica gel, eluting with 2% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-77786d6651e545b5b9146ffe454cfdf6
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071365B2

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