4-(Hydroxymethyl)benzeneboronic acid → 1-[2-(4-Hydroxymethylphenyl)cyclopenten-1-yl]-4-(methylthio)benzene

HRID 2226001노트

반응식

HRID 2226001 반응식
Br[C:2]1[CH2:6][CH2:5][CH2:4][C:3]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1.[OH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1>>[OH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH2:6][CH2:5][CH2:4][C:3]=2[C:7]2[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=2)=[CH:19][CH:18]=1

참가 물질

3

반응물 2

HCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 102650591-(2-Bromocyclopenten-1-yl)-4-(methylthio)benzene

생성물 1

HCID 229172821-[2-(4-Hydroxymethylphenyl)cyclopenten-1-yl]-4-(methylthio)benzene수율 92.5%

실험 절차

Following the synthetic procedure outlined in Step 3 of Example 1, 250 mg (0.93 mmol) of 1-(2-bromocyclopenten-1-yl) -4-(methylthio) benzene (Example 1, Step 2) was reacted with 290 mg (1.9 mmol) of 4-hydroxymethylphenylboronic acid (Step 1). Purification by silica gel chromatography (MPLC) with ethyl acetate/hexane (1:4) gave 255 mg (92%) of 1-[2-(4-hydroxymethylphenyl)cyclopenten-1-yl]-4-(methylthio)benzene as a solid: mp 82°-85° C.; NMR (CDCl3) d 2.04 (m, J=7 Hz, 2H) , 2.45 (s, 3H) , 2.88 (t, J=7 Hz, 4H) , 4.64 (s, 2H) , 7.08 (s, 4H) , (m, 2H) , 7.15-7.25 (m, 4H) .

후처리

  1. customPurification by silica gel chromatography (MPLC) with ethyl acetate/hexane (1:4)

출처 및 근거

ORD 기록
ord-b7662eb84b6e4d9988d97b9a5183e4ef
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05344991

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