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

HRID 1836884노트

반응식

HRID 1836884 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

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.).

후처리

  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)

출처 및 근거

ORD 기록
ord-6acc282be1a449eb8c6ed8231e07f8aa
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06777418B2

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