Pyridine → Phenyl [4-(tetradecyloxy)phenyl]methyl carbonate

HRID 248002

반응식

HRID 248002 반응식
[CH2:1]([O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][OH:21])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].N1C=CC=CC=1.Cl[C:31]([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:32].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:31](=[O:32])([O:21][CH2:20][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:23][CH:22]=1)[O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 100873844-Tetradecyloxybenzyl alcohol

생성물 1

HCID 10411003Phenyl [4-(tetradecyloxy)phenyl]methyl carbonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a 0° C. mixture of 9.0 g of product from Example 19, 4.44 g of pyridine and 70 ml of methylene chloride is added, dropwise, 5.28 of phenyl chloroformate. The reaction is stirred at 0° C. for 15 minutes; followed by room temperature for 30 minutes. The mixture is poured into saturated sodium bicarbonate and the aqueous layer is extracted with methylene chloride. The combined organic layers are washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel: 0-5% ethyl acetate/hexane) to give 12.6 g of colorless prisms.

후처리

  1. additionis added
  2. waitfollowed by room temperature for 30 minutes
  3. extractionthe aqueous layer is extracted with methylene chloride
  4. washThe combined organic layers are washed with saturated sodium chloride
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by column chromatography (silica gel: 0-5% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-f74921ea5ccd4e1e8f1a6b2340757ce0
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05208247

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