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

HRID 1160300ノート

反応式

HRID 1160300 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8acf5ee8229241c383bd17f42947fa03
出典データセット
uspto-grants-2010_10
特許番号
US07816367B2

反応ノート

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