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

HRID 1993049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1993049
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a105c77590f145fb9d3b48f8453aa248
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07649110B2

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