Acetic Acid → 3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthalenecarboxaldehyde

HRID 1836862

반응식

HRID 1836862 반응식
[C:1]([C:3]1[C:12]([CH3:13])=[CH:11][C:10]2[C:9]([CH3:15])([CH3:14])[CH2:8][CH2:7][C:6]([CH3:17])([CH3:16])[C:5]=2[CH:4]=1)#N.[H-].C([Al+]CC(C)C)C(C)C.C(O)(=[O:30])C.O>ClCCl>[CH:1]([C:3]1[C:12]([CH3:13])=[CH:11][C:10]2[C:9]([CH3:15])([CH3:14])[CH2:8][CH2:7][C:6]([CH3:17])([CH3:16])[C:5]=2[CH:4]=1)=[O:30]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 962WaterHCID 35534396-Cyano-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthaleneHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 2266983,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthalenecarboxaldehyde수율 63%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 18.7 g (82.3 mmol) of 2-cyano-3-methyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene in 280 mL of dichloromethane, cooled at −78°, was added 123 mL (123 mmol) of diisobutyl aluminum hydride (1.0 M in toluene). The reaction mixture was stirred and allowed to gradually warm to room temperature. After 16 hours, the reaction mixture was treated with 30 mL of acetic acid added dropwise, followed by 150 mL of water. The organic layer was separated, diluted with 200 mL of hexane, washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution 5-10% ethyl acetate/hexane) on silica gel to afford 11.8 g (63%) of 2-formyl-3-methyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene.

후처리

  1. additionadded dropwise
  2. customThe organic layer was separated
  3. additiondiluted with 200 mL of hexane
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (gradient elution 5-10% ethyl acetate/hexane) on silica gel

출처 및 근거

ORD 기록
ord-c7bdc6b501db4b338bc1f72659249bd2
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06777418B2

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