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Sodium borohydride → Methyl 2-hydroxy-4-[3-hydroxy-3-(5,6,7,8-tetrahydro-5,6,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate

HRID 861766
ノート
印刷プレビュー

反応式

HRID 861766 の反応式
[OH:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][C:14](=[O:29])[C:15]2[CH:24]=[CH:23][C:22]3[C:21](C)([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=3[CH:16]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CO.[CH2:32]1COCC1.[BH4-].[Na+]>O>[OH:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][CH:14]([OH:29])[C:15]2[CH:24]=[CH:23][C:22]3[CH:21]([CH3:25])[CH:20]([CH3:32])[CH2:19][C:18]([CH3:27])([CH3:28])[C:17]=3[CH:16]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 4311764Sodium borohydrideHCID 15285826Methyl 2-hydroxy-4-[3-oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoateHCID 21899815MeOH tetrahydrofuran

生成物 1

HCID 19700225Methyl 2-hydroxy-4-[3-hydroxy-3-(5,6,7,8-tetrahydro-5,6,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

2.9 g (7.4 mmol) of methyl 2-hydroxy-4-[3-oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate and 100 ml of a methanol/THF (50/50) mixture were introduced into a round-bottomed flask and 140 mg (3.7 mmol) of sodium borohydride were added in small amounts. The reaction mixture was stirred at room temperature for 2 hours, poured into water and extracted with ethyl ether. The organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with a mixture of dichloromethane and hexane (50/50). After evaporation of the solvents, 1.6 g (55%) of the expected compound, with a melting point of 92°-93° C., was recovered.

後処理

  1. extractionextracted with ethyl ether
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customwas purified by chromatography on a silica column
  7. washeluted with a mixture of dichloromethane and hexane (50/50)
  8. customAfter evaporation of the solvents, 1.6 g (55%) of the expected compound
  9. customwith a melting point of 92°-93° C., was recovered

出典と根拠

ORDレコード
ord-5a53f3391e9d426ab9ebd166208c1048
出典データセット
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05716624

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート