Hydrochloric Acid → Methyl 3-[4-(4-pentylphenyl)phenyl]acrylate

HRID 1872362노트

반응식

HRID 1872362 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:19]([O:23][CH3:24])(=[O:22])[CH:20]=[CH2:21].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Cl>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[CH2:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH:21]=[CH:20][C:19]([O:23][CH3:24])=[O:22])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)[CH2:15][CH2:16][CH2:17][CH3:18]

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 6187094-Bromo-4'-pentylbiphenyl

생성물 1

HCID 54407370Methyl 3-[4-(4-pentylphenyl)phenyl]acrylate

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 4-bromo-4'-pentylbiphenyl (5.0 g), methyl acrylate (2.2 ml), palladium acetate (0.11 g) and tris(o-tolyl)phosphine (0.60 g) in triethylamine (16 ml) was refluxed for 15 hours under nitrogen atmosphere. The reaction mixture was poured into a mixture of cold water and ethyl acetate, and adjusted to about pH 1.5 with 6N hydrochloric acid. The separated organic layer was washed in turn with water and brine, and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give a crude powder, which was subjected to column chromatography on silica gel (200 ml), and eluted with a mixture of (n-hexane:ethyl acetate=100:0-93:6, V/V) to give Methyl 3-[4-(4-pentylphenyl)phenyl]acrylate (4.48 g).

후처리

  1. temperaturewas refluxed for 15 hours under nitrogen atmosphere
  2. washThe separated organic layer was washed in turn with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. customthe filtrate was evaporated under reduced pressure
  6. customto give a crude powder, which
  7. washeluted with a mixture of (n-hexane:ethyl acetate=100:0-93:6, V/V)

출처 및 근거

ORD 기록
ord-d52b9d80b482406980f83cc9b981b6d5
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06107458

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