Sodium Chloride → Allyl 3-[1-(4-allyloxycarbonyl-4-methylcyclohexyl)methoxy]-4-methoxycinnamate

HRID 2225502

반응식

HRID 2225502 반응식
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH:9]1[CH2:14][CH2:13][C:12]([CH3:21])([C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])[CH2:11][CH2:10]1.[OH:22][C:23]1[CH:24]=[C:25]([CH:34]=[CH:35][C:36]=1[O:37][CH3:38])[CH:26]=[CH:27][C:28]([O:30][CH2:31][CH:32]=[CH2:33])=[O:29].OC1C=C(C=CC=1OC)C=CC(O)=O.[Cl-].[Na+]>CN(C=O)C>[CH2:18]([O:17][C:15]([C:12]1([CH3:21])[CH2:13][CH2:14][CH:9]([CH2:8][O:22][C:23]2[CH:24]=[C:25]([CH:34]=[CH:35][C:36]=2[O:37][CH3:38])[CH:26]=[CH:27][C:28]([O:30][CH2:31][CH:32]=[CH2:33])=[O:29])[CH2:10][CH2:11]1)=[O:16])[CH:19]=[CH2:20]

참가 물질

7

반응물 5

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 921263-(3-Hydroxy-4-methoxyphenyl)prop-2-enoic acidHCID 19004693Allyl 4-iodomethyl-methyl-1-cyclohexanecarboxylateHCID 54483065Allyl 3-hydroxy-4-methoxycinnamate

생성물 1

HCID 53660565Allyl 3-[1-(4-allyloxycarbonyl-4-methylcyclohexyl)methoxy]-4-methoxycinnamate수율 47.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5 g of potassium carbonate and 1.1 g of allyl 4-iodomethyl-methyl-1-cyclohexanecarboxylate (Example 46) were added to a solution of 0.8 g of allyl 3-hydroxy-4-methoxycinnamate, derived from 3-hydroxy-4-methoxycinnamic acid by the allyl-esterification thereof, in 50 ml of DMF. The solution was reacted for 18 hours at 100° C. After reaction, 100 ml of an aqueous sodium chloride solution was added to the reaction solution. The solution was extracted three times with 50 ml of ethyl acetate. The organic layer obtained was washed three times with an aqueous sodium chloride solution and was dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo. The oily substance obtained was subjected to column chromatography using 5 g of silica gel. From the fraction eluted with hexane and ethyl acetate=2:1, the solvent was removed in vacuo, yielding 0.7 g of allyl 3-[1-(4-allyloxycarbonyl-4-methylcyclohexyl)methoxy]-4-methoxycinnamate (a compound of the present invention) as a pale yellow oil, which had the following physiochemical properties:

후처리

  1. customThe solution was reacted for 18 hours at 100° C
  2. additionwas added to the reaction solution
  3. extractionThe solution was extracted three times with 50 ml of ethyl acetate
  4. customThe organic layer obtained
  5. washwas washed three times with an aqueous sodium chloride solution
  6. dry with materialwas dried over magnesium sulfate
  7. customThereafter, the solvent was removed in vacuo
  8. customThe oily substance obtained
  9. washFrom the fraction eluted with hexane and ethyl acetate=2:1
  10. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-b72f1d0f28b24e76b206ef87c3772fc8
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05344845

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