2-Nitropropane → 3-Fluoro-2-formyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene

HRID 1836884ノート

反応式

HRID 1836884 の反応式
[N+](C(C)C)([O-])=[O:2].[Na].[F:8][C:9]1[C:18]([CH2:19]Br)=[CH:17][C:16]2[C:15]([CH3:22])([CH3:21])[CH2:14][CH2:13][C:12]([CH3:24])([CH3:23])[C:11]=2[CH:10]=1>C(O)C>[F:8][C:9]1[C:18]([CH:19]=[O:2])=[CH:17][C:16]2[C:15]([CH3:22])([CH3:21])[CH2:14][CH2:13][C:12]([CH3:24])([CH3:23])[C:11]=2[CH:10]=1

参加物

5

反応物 3

HCID 3982-NitropropaneHCID 5360545SodiumHCID 234988892-Fluoro-3-bromomethyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

生成物 1

HCID 234989783-Fluoro-2-formyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene収率 58%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

5.26 g (59.0 mmol) of 2-nitropropane was added to a solution prepared by dissolving 1.04 g (45.4 mmol) of sodium in 60 mL of ethanol. The resulting solution was added to a solution of 16.9 g (45.4 mmol) of crude 2-fluoro-3-bromomethyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene in 60 mL of ethanol. After 5 hours the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with 1M aqueous sodium hydroxide, water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The product was purified by flash chromatography on silica gel (1% ethyl acetate/hexane) to afford 6.17 g (58%) of 3-fluoro-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehyde (m.p.=119.4-120.0° C.).

後処理

  1. customprepared
  2. customAfter 5 hours the reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with 1M aqueous sodium hydroxide, water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by flash chromatography on silica gel (1% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-6acc282be1a449eb8c6ed8231e07f8aa
出典データセット
uspto-grants-2004_08
特許番号
US06777418B2

反応ノート

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