[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide → HCID 68977946, 화합물

HRID 1866452노트

반응식

HRID 1866452 반응식
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][O:15][CH3:16])[CH:8]=O.[Br-].[CH3:18][O:19][C:20]([C:22]1[CH:47]=[CH:46][C:25]([CH2:26][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:24][CH:23]=1)=[O:21].[O-][CH2:49]C.[Li+]>CCO>[CH2:18]([O:19][C:20](=[O:21])[C:22]1[CH:47]=[CH:46][C:25]([CH:26]=[CH:8][C:7]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][O:15][CH3:16])=[C:5]([O:4][CH2:3][O:2][CH3:1])[CH:6]=2)=[CH:24][CH:23]=1)[CH3:49]

참가 물질

5

반응물 3

HCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromideHCID 117463143,4-Bis(methoxymethoxy)benzaldehydeHCID 23661847Lithium ethoxide

생성물 1

HCID 68977946HCID 68977946, 화합물수율 99%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a mixture of 3,4-bis-methoxymethoxy-benzaldehyde (100 mmol) and (4-methoxycarbonyl-benzyl)-triphenyl-phosphonium bromide (100 mmol) in of EtOH (300 mL) at 0° C. was added slowly of a lithium ethoxide solution (101 mL, 1 M in EtOH). Upon the completion of the addition, the cold bath was removed and the reaction was allowed to warm to room temperature. The stirring was continued for additional 2 h. The solvent was then removed by rotary evaporation and residue was taken up to 500 mL of EtOAc and washed with ammonium chloride solution (2×100 mL) and water. The organic layer was dried over Na2SO4 and the crude product was purified on silica (hexane:EtOAc=2:1) to afford a clear sticky solid (yield 99%). NMR indicated the purified product is a mixture of cis/trans isomers containing ethyl and methyl esters. 1H-NMR (300 MHz, CDCl3) δ 8.02 (d, J=0.84, 1.5H), 7.93 (d, J=0.84, 0.5H), 7.91 (s, 0.3H), 7.55 (s, 0.75H), 7.52 (s, 0.75H), 7.38-7.33 (m, 1.25H), 7.17-7.12 (m, 2.25H), 7.03-6.98 (m, 1.25H), 6.84 (m, 0.25H), 6.61-6.52 (m, 0.5H), 5.29-5.05 (m, 4H), 4.41-4.25 (m, 1H), 3.90 (s, 1.5H), 3.56-3.39 (m, 6H), 1.40 (q, J=6 Hz, 1.5H).

후처리

  1. additionUpon the completion of the addition
  2. customthe cold bath was removed
  3. customThe solvent was then removed by rotary evaporation and residue
  4. washwashed with ammonium chloride solution (2×100 mL) and water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customthe crude product was purified on silica (hexane:EtOAc=2:1)

출처 및 근거

ORD 기록
ord-e70e411fba2643d89b45b7cb4c512fd7
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07629375B2

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