Vertellus → 3-Methyl-2-phenyl-1-naphthalenol

HRID 1992986노트

반응식

HRID 1992986 반응식
CC1C=CC(S(O[C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][C:16]([CH3:29])=[C:17]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:18]=3[OH:22])[CH:13]=2)(=O)=O)=CC=1.[B-].[Na+]>C(Cl)(Cl)Cl.CO.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:29][C:16]1[C:17]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:18]([OH:22])[C:19]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:21][CH:20]=2

참가 물질

6

반응물 2

HCID 22959485VertellusHCID 866166715-Hydroxy-7-methyl-6-phenyl-2-naphthalenyl 4-methylbenzenesulfonate

생성물 1

HCID 685367573-Methyl-2-phenyl-1-naphthalenol수율 44.1%

시약·촉매·용매 3

HCID 11791229Dichloronickel;hexahydrate촉매HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

To a cold (5° C.) solution of 5-hydroxy-7-methyl-6-phenyl-2-naphthalenyl 4-methylbenzenesulfonate (239) (0.250 g, 0.62 mmol) in CHCl3 (5 mL) and MeOH (5 mL) was added nickel chloride hexahydrate (0.238 g, 1.24 mmol). To the above mixture sodium borohydrate (0.471 g, 12.4 mmol) was added portion-wise. The resulting black mixture was stirred at that temperature for 15 min. Reaction mixture was filtered through a pad of celite (washings were done with CHCl3). The filtrate was concentrated under reduced pressure to afford the crude product. The product was purified by column chromatography to afford 0.064 g (44%) of the title compound (86) as an oil. 1H NMR (400 MHz, CDCl3): δ 8.22 (d, J=8.0 Hz, 1H), 7.77 (d, J=8.0 Hz, 1H), 7.59-7.55 (m, 2H), 7.52-7.46 (m, 3H), 7.40-7.36 (m, 3H), 5.28 (s, 1H), 2.22 (s, 3H). LCMS (ESI) m/z (M+H)+.

후처리

  1. customReaction mixture
  2. filtrationwas filtered through a pad of celite (washings were done with CHCl3)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto afford the crude product
  5. customThe product was purified by column chromatography

출처 및 근거

ORD 기록
ord-f6db188b19c94520a5a43a3ffbbe77a0
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07649093B2

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