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

HRID 1160300Notes

Reaction equation

HRID 1160300 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8acf5ee8229241c383bd17f42947fa03
Source dataset
uspto-grants-2010_10
Patent number
US07816367B2

Reaction notes

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