Methane → 3-Acetoacetoxyadamantan-1-yl methacrylate

HRID 1910373

반응식

HRID 1910373 반응식
[C:1]([O:6][C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][C:9]([OH:17])([CH2:10]3)[CH2:8]1)[CH2:14]2)(=[O:5])[C:2]([CH3:4])=[CH2:3].CC1(C)[O:24][C:23](=O)[CH:22]=[C:21]([CH3:26])[O:20]1.C>C1(C)C=CC=CC=1.COP(OC1C=CC(C#N)=CC=1)(OC)=S>[C:1]([O:6][C:7]12[CH2:14][CH:13]3[CH2:12][CH:11]([CH2:10][C:9]([O:17][C:23](=[O:24])[CH2:22][C:21]([CH3:26])=[O:20])([CH2:15]3)[CH2:8]1)[CH2:16]2)(=[O:5])[C:2]([CH3:4])=[CH2:3]

참가 물질

6

반응물 3

HCID 297MethaneHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-oneHCID 118565233-Hydroxy-1-methacryloyloxyadamantane

생성물 1

HCID 866740743-Acetoacetoxyadamantan-1-yl methacrylate수율 90%

시약·촉매·용매 2

HCID 17522Cyanophos촉매HCID 1140Toluene용매2회

반응 조건

온도
110 °C

실험 절차

3-(Acetoacetyloxy)adamantyl methacrylate (AAHAMA) was prepared according to the following procedure. 65.6 g of 3-hydroxyadamantan-1-yl methacrylate (HAMA) (277.6 mmol) and 42.1 g of 95% pure 2,2,6-trimethyl-4H-1,3-dioxin-4-one (277.6 mmol) were mixed with 0.2 g of CYANOX® 1790 inhibitor in 400 ml of toluene. After refluxing (110° C.) for 4 hours, the reaction was cooled, 10 g of activated charcoal and 400 ml of toluene were added, and the mixture stirred overnight. After filtration, another 10 g of activated charcoal was added, and the mixture stirred for an additional 12 h., then filtered. The filtrate was concentrated and run through a silica gel flash column with ethyl acetate as eluant. The solvent was then removed to yield 80 g (90%) of 3-acetoacetoxyadamantan-1-yl methacrylate was obtained.

후처리

  1. custom3-(Acetoacetyloxy)adamantyl methacrylate (AAHAMA) was prepared
  2. temperaturethe reaction was cooled
  3. filtrationAfter filtration
  4. additionanother 10 g of activated charcoal was added
  5. stirringthe mixture stirred for an additional 12 h.
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customThe solvent was then removed

출처 및 근거

ORD 기록
ord-edabee4ed837410b9a8adf9a2ea4f15d
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08603728B2

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