Methanol → 4-[2-Methyl-4-(2-methyl-benzyloxy)-phenyl]-but-3-en-2-ol

HRID 1160300노트

반응식

HRID 1160300 반응식
[BH4-].[Na+].CO.[CH3:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH:9]=[CH:8][C:7]=1[CH:21]=[CH:22][C:23](=[O:25])[CH3:24]>C1COCC1>[CH3:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH:9]=[CH:8][C:7]=1[CH:21]=[CH:22][CH:23]([OH:25])[CH3:24]

참가 물질

5

반응물 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 686742184-[2-Methyl-4-(2-methyl-benzyloxy)-phenyl]-but-3-en-2-one

생성물 1

HCID 686760914-[2-Methyl-4-(2-methyl-benzyloxy)-phenyl]-but-3-en-2-ol수율 94%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

NaBH4 (20 mg, 0.51 mmol) was added to a 0.4 M solution of CeCl3 in MeOH (0.65 mL, 0.26 mmol), 31.4 (74 mg, 0.26 mmol), and THF (1 mL). The reaction was stirred, uncapped, until gas evolution ceased. The reaction was quenched with water (1.5 mL) and partitioned between water and diethyl ether. The aqueous layer was extracted 2 times with diethyl ether and the combined organic layers were washed with brine and concentrated in vacuo to yield 69 mg (93%) of 4-[2-Methyl-4-(2-methyl-benzyloxy)-phenyl]-but-3-en-2-ol (31.5). LC/MSD m/e: 266.3 (M−OH); 1H NMR (400 MHz) (DMSO-d6) δ 7.44 (2H, m), 7.25 (3H, m0, 6.86 (2H, m), 6.75 (1H, m), 6.08 (1H, m), 5.11 (2H, s), 4.40, (1H, m), 2.38 (3H, s), 2.32 (3H, s), 1.29 (3H, m).

후처리

  1. customThe reaction was quenched with water (1.5 mL)
  2. custompartitioned between water and diethyl ether
  3. extractionThe aqueous layer was extracted 2 times with diethyl ether
  4. washthe combined organic layers were washed with brine
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8acf5ee8229241c383bd17f42947fa03
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816367B2

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