1,1,3,3-Tetramethylguanidine → (3E)-3-[[3,5-dimethyl-4-(phenylmethoxy)phenyl]methylene]-1,4-dioxaspiro[4.5]decan-2-one

HRID 642907

반응식

HRID 642907 반응식
[Cl-].[Li+].[CH2:3]([O:10][C:11]1[C:18]([CH3:19])=[CH:17][C:14]([CH:15]=O)=[CH:13][C:12]=1[CH3:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OP([CH:29]1[C:33](=[O:34])[O:32][C:31]2([CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)[O:30]1)(=O)OCC)C.CN(C)C(=N)N(C)C>O1CCCC1.C(OC)(C)(C)C>[CH3:20][C:12]1[CH:13]=[C:14](/[CH:15]=[C:29]2\[C:33](=[O:34])[O:32][C:31]3([CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)[O:30]\2)[CH:17]=[C:18]([CH3:19])[C:11]=1[O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

7

반응물 4

HCID 664601,1,3,3-TetramethylguanidineHCID 433294Lithium ChlorideHCID 5635574-(Benzyloxy)-3,5-dimethylbenzaldehydeHCID 59259703Diethyl(3-oxo-1,4-dioxaspiro[4.5]dec-2-yl)-phosphonate

생성물 1

HCID 59259697(3E)-3-[[3,5-dimethyl-4-(phenylmethoxy)phenyl]methylene]-1,4-dioxaspiro[4.5]decan-2-one

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 15413tert-Butyl methyl ether용매

반응 조건

온도
-20 °C

실험 절차

4.2 g lithium chloride (0.1 Mol), 20.0 g (83.2 mmol) of 4-benzyloxy-3,5-dimethylbenzaldehyde (D) and 31.62 g (108.2 mmol) of diethyl (3-oxo-1,4-dioxaspiro[4.5]dec-2-yl)-phosphonate (C) are suspended in 130 mL tetrahydrofuran and cooled to −20° C. At this temperature 12.5 mL (0.1 Mol) tetramethylguanidine are added dropwise. After the addition has ended the suspension formed is heated to ambient temperature and stirred for 1 hour. After the addition of 190 mL tert.butyl-methylether the organic phase is washed with 150 mL water and 30 mL saturated saline solution, dried and evaporated down. The resulting yellow oil is taken up in 145 mL methanol and stirred intensively for 1 hour at −10° C., during which time a white solid is formed. The solid formed is suction filtered, washed twice with 20 mL methanol/water (1:1) and dried at 45° C. Yield: 26.0 g (86% of theory)

후처리

  1. additionAfter the addition
  2. customformed
  3. temperatureis heated to ambient temperature
  4. washis washed with 150 mL water and 30 mL saturated saline solution
  5. customdried
  6. customevaporated down
  7. stirringstirred intensively for 1 hour at −10° C., during which time a white solid
  8. customis formed
  9. customThe solid formed
  10. filtrationfiltered
  11. washwashed twice with 20 mL methanol/water (1:1)
  12. customdried at 45° C

출처 및 근거

ORD 기록
ord-16fd93c7bd8a42bfa0db4fd191f28a52
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696346B2

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