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

HRID 1992986ノート

反応式

HRID 1992986 の反応式
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

参加物

6

反応物 2

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

生成物 1

HCID 685367573-Methyl-2-phenyl-1-naphthalenol収率 44.1%

試薬・触媒・溶媒 3

HCID 11791229Dichloronickel;hexahydrate触媒HCID 887Methanol溶媒HCID 6212Chloroform溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-f6db188b19c94520a5a43a3ffbbe77a0
出典データセット
uspto-grants-2010_01
特許番号
US07649093B2

反応ノート

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