Tri-o-tolylphosphine → Ethyl (E)-4-[2-(5,6,7,8-tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethenyl]-benzoate

HRID 481199

반응식

HRID 481199 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[CH:15]([C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1)=[CH2:16].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:13][C:6]1([CH3:14])[CH2:7][CH2:8][C:9](=[O:12])[C:10]2[CH:11]=[C:2](/[CH:16]=[CH:15]/[C:17]3[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=3)[CH:3]=[CH:4][C:5]1=2

참가 물질

6

반응물 3

HCID 80271Tri-o-tolylphosphineHCID 107533577-Bromo-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-one2회HCID 10866858Ethyl 4-vinylbenzoate

생성물 1

HCID 12069038Ethyl (E)-4-[2-(5,6,7,8-tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethenyl]-benzoate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8471Triethylamine용매

반응 조건

온도
95 °C

실험 절차

To a solution of 520.0 mg (2.00 mmol) of 3,4-dihydro-4,4-dimethyl-7-bromo-naphthalen-1(2H)-one (Compound G), and 510.0 mg (2.90 mmol) of ethyl 4-vinylbenzoate in 4.0 mL of triethylamine (degassed by sparging with argon for 25 minutes), was added 124.0 mg (0.40 mmol) of tris(2-methylphenyl) phosphine, followed by 44.0 mg (0.20 mmol) of palladium(II)acetate. The resulting solution was heated to 95° C. for 2.5 h, cooled to room temperature, and concentrated under reduced pressure. Purification by column chromatography (10% EtOAc/hexanes) afforded the title compound as a colorless solid.

후처리

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customPurification by column chromatography (10% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-0b024d96a65c45d99daf9b8aa13144fc
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06653483B1

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