1-Octanol → Octyl4'-methoxycarbonyloxy-4-biphenylcarboxylate

HRID 651303

반응식

HRID 651303 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][O:21][C:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([OH:39])=[O:38])=[CH:33][CH:32]=2)=[CH:27][CH:26]=1)=[O:23].[CH2:40](O)[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:20][O:21][C:22]([O:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[O:38])=[CH:33][CH:32]=2)=[CH:29][CH:30]=1)=[O:23]

참가 물질

6

반응물 4

HCID 9571-OctanolHCID 11776Triphenylphosphine2회HCID 220568ethyl N-ethoxycarbonyliminocarbamate2회HCID 183284084'-Methoxycarbonyloxy-4-biphenylcarboxylic acid2회

생성물 1

HCID 18328376Octyl4'-methoxycarbonyloxy-4-biphenylcarboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of triphenylphosphine (3.78 g, 0.014 mol) in dry tetrahydrofuran (50 ml) was added to a stirred solution of compound 4 (3.92 g, 0.014 mol), octan-1-ol (1.88 g 0.014 mol) and diethyl azodicarboxylate (DEAD) (2.51 g 0.014 mol) in dry tetrahydrofuran (100 ml) under an atmosphere of dry nitrogen. The addition was such that the triphenylphosphine was added over 30 seconds in which time the solution became hot and the white solid (4) and orange colour (DEAD) disappeared. The resultant solution was stirred overnight, the solvent was removed in vacuo and the viscous, oily residue was purified by column chromatography (10% petrol/dichloromethane) to give a colourless solid which was recrystallised from ethanol to leave colourless plates.

후처리

  1. additionThe addition
  2. additionwas added over 30 seconds in which time the solution
  3. customthe solvent was removed in vacuo
  4. customthe viscous, oily residue was purified by column chromatography (10% petrol/dichloromethane)
  5. customto give a colourless solid which
  6. customwas recrystallised from ethanol
  7. customto leave colourless plates

출처 및 근거

ORD 기록
ord-21b90c025f3a4e54907e42cc3e272c2f
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06278028B1

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