Water → 6-tert-Butyl-5-methoxy-2-methyl-4-phenylindan-1-one

HRID 716441노트

반응식

HRID 716441 반응식
Br[C:2]1[C:10]([O:11][CH3:12])=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH3:18])[C:6]2=[O:17].C([O-])([O-])=O.[Na+].[Na+].[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[C:13]([C:9]1[CH:8]=[C:7]2[C:3]([CH2:4][CH:5]([CH3:18])[C:6]2=[O:17])=[C:2]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:10]=1[O:11][CH3:12])([CH3:16])([CH3:15])[CH3:14]

참가 물질

8

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 602106934-Bromo-6-tert-butyl-5-methoxy-2-methyl-1-indanone

생성물 1

HCID 712309196-tert-Butyl-5-methoxy-2-methyl-4-phenylindan-1-one수율 98%

시약·촉매·용매 3

HCID 11776Triphenylphosphine촉매HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a mixture of 46.7 g (0.150 mol) of 4-bromo-6-tert-butyl-5-methoxy-2-methylindan-1-one, 44.5 g (0.420 mol) of Na2CO3, 22.0 g (0.180 mol) of PhB(OH)2, 570 ml of DME, and 195 ml of water 0.674 g (3.0 mmol) of Pd(OAc)2 and 1.58 g (6.00 mmol) of PPh3 were added. The resulting mixture was refluxed for 12 h, cooled to room temperature, and then DME was evaporated on Rotavap. To the residue 1 liter of cold water was added, and the crude product was extracted with 3×300 ml of dichloromethane. The combined organic extract was dried over K2CO3 and then evaporated to dryness. The residue after evaporation was extracted with hot hexane (500 ml, then 3×250 ml) and this extracts while hot were passed through a short pad of silicagel, evaporated on Rotavap to yield 45.1 g (98%) of 6-tert-butyl-5-methoxy-2-methyl-4-phenylindan-1-one as a slightly yellowish crystalline solid which was further used without an additional purification.

후처리

  1. additionwere added
  2. temperatureThe resulting mixture was refluxed for 12 h
  3. customDME was evaporated on Rotavap
  4. additionTo the residue 1 liter of cold water was added
  5. extractionthe crude product was extracted with 3×300 ml of dichloromethane
  6. extractionThe combined organic extract
  7. dry with materialwas dried over K2CO3
  8. customevaporated to dryness
  9. customThe residue after evaporation
  10. extractionwas extracted with hot hexane (500 ml
  11. customevaporated on Rotavap

출처 및 근거

ORD 기록
ord-e60303ce81dc43329d2cf11be60516c9
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187583B2

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