2-[4-[(4-Methoxyphenyl)methyl]phenyl]oxazole → 4-[[4-(2-Oxazolyl)phenyl]methyl]phenol

HRID 1046316

반응식

HRID 1046316 반응식
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[O:17][CH:18]=[CH:19][N:20]=3)=[CH:12][CH:11]=2)=[CH:5][CH:4]=1>ClCCl>[O:17]1[CH:18]=[CH:19][N:20]=[C:16]1[C:13]1[CH:12]=[CH:11][C:10]([CH2:9][C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)=[CH:15][CH:14]=1

참가 물질

3

반응물 1

HCID 684889492-[4-[(4-Methoxyphenyl)methyl]phenyl]oxazole

생성물 1

HCID 684892774-[[4-(2-Oxazolyl)phenyl]methyl]phenol수율 58.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 2-[4-[(4-methoxyphenyl)methyl]phenyl]oxazole (0.4 g, 1.5 mmol) in dichloromethane (15 mL) was stirred and cooled to −78° C. as a solution of borontribromide in dichloromethane (1 N, 15 mL, 15 mmol) was added over 5 minutes. The cooling bath was removed and the reaction was allowed to warm to ambient temperature over 3 days. The reaction was diluted with methanol and concentrated, repeat twice. Purification on silica gel using a gradient of ethyl acetate in dichloromethane and hexane gave 0.22 g of 4-[[4-(2-oxazolyl)phenyl]methyl]phenol, 1H NMR (400 MHz, DMSO-d6) δ 9.19 (S, 1H), 8.17 (s, 1H), 7.88 (s, 2H), 7.35 (d, 2H), 7.02 (s, 2H), 6.66 (d, 2H), 3.84 (s, 2H).

후처리

  1. additionwas added over 5 minutes
  2. customThe cooling bath was removed
  3. additionThe reaction was diluted with methanol
  4. concentrationconcentrated
  5. customPurification on silica gel using a gradient of ethyl acetate in dichloromethane and hexane

출처 및 근거

ORD 기록
ord-257de4d76036434ab665b7cea5eff1c1
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569303B2

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