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

HRID 1993049노트

반응식

HRID 1993049 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-a105c77590f145fb9d3b48f8453aa248
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07649110B2

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