Triphenylphosphine → 3-(3-Hydroxy-4-methoxyphenyl)propanal

HRID 2414991

반응식

HRID 2414991 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12](O)=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C(OC(=O)C(C)(C)C)(=O)C(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[H][H]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCCC1>[OH:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][CH:12]=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 15234Pivalic anhydrideHCID 27520543-Hydroxy-4-methoxybenzenepropanoic acidHCID 178418361HCID 178418361, 화합물2회

생성물 1

HCID 98154073-(3-Hydroxy-4-methoxyphenyl)propanal수율 48.3%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

To a chemical reactor for hydrogenation under elevated pressure, 3-(3-hydroxy-4-methoxyphenyl)propionic acid (5.09 g, 25.9 mmol), pivalic acid anhydride (14.3 g, 76.6 mmol) and tetrahydrofuran (64 ml) were introduced, and thereafter the mixture was bubbled with nitrogen gas for 10 minutes. Palladium acetate (57 mg, 0.254 mmol) and triphenyl phosphine (349 mg, 1.33 mmol) were added thereto, and the mixture was bubbled with nitrogen gas for 20 minutes to substitute nitrogen gas completely for the gas in the system of reaction, whereby the system was filled with nitrogen gas. Next, hydrogen gas was added thereinto to substitute hydrogen gas for the gas in the system, and then the mixture was stirred under hydrogen pressure of 5.4 MPa at 80° C. for 24 hours for reaction. Thus obtained reaction solution was concentrated under reduced pressure to remove tetrahydrofaran by distillation. The remaining residue was purified with a silica gel column chromatography. The eluted fractions containing the object compound were concentrated under reduced pressure to obtain crude 3-(3-hydroxy-4-methoxyphenyl)propionaldehyde (2.26 g, 12.5 mmol, yield: 48%) in a slightly yellow colored solid form.

후처리

  1. customthe mixture was bubbled with nitrogen gas for 10 minutes
  2. customthe mixture was bubbled with nitrogen gas for 20 minutes
  3. customin the system of reaction, whereby the system
  4. additionwas filled with nitrogen gas
  5. customfor reaction
  6. customThus obtained reaction solution
  7. concentrationwas concentrated under reduced pressure
  8. customto remove tetrahydrofaran
  9. distillationby distillation
  10. customThe remaining residue was purified with a silica gel column chromatography
  11. additionThe eluted fractions containing the object compound
  12. concentrationwere concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-7924cc89ff914dfc81d1c634aa20772e
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06818243B2

연결된 노트

불러오는 중…