聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 白藜芦醇

HRID 885081

反应方程式

HRID 885081 反应方程式
[Br-].C[O:3][C:4]1[CH:29]=[CH:28][C:7]([CH2:8][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:6][CH:5]=1.C([Li])CCC.C[O:36][C:37]1[CH:38]=[C:39]([CH:42]=[C:43]([O:45]C)[CH:44]=1)[CH:40]=O.O>O1CCCC1>[OH:3][C:4]1[CH:5]=[CH:6][C:7](/[CH:8]=[CH:40]/[C:39]2[CH:42]=[C:43]([OH:45])[CH:44]=[C:37]([OH:36])[CH:38]=2)=[CH:28][CH:29]=1

参与物

6

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 817473,5-二甲氧基苯甲醛HCID 27348854-甲氧基苄基三苯基膦溴化盐HCID 178418339正丁基锂

产物 1

HCID 445154白藜芦醇收率 86%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂2 次

实验过程

To a solution of 4-methoxy-benzyltriphenylphosphonium bromide (12.5 g) in anhydrous tetrahydrofuran (200 mL) at −78° C. was added n-butyllithium (2.44 M, 1.0 equiv), and the resulting red solution was stirred under argon for 2-4 h. A solution of 3,5-dimethoxybenzaldehyde (4.5 g) in tetrahydrofuran was added dropwise over 30 min and the mixture stirred for 6-15 h. The resulting cream suspension was poured into water and extracted with dichloromethane. The organic phase was washed with water, and removal of the solvent in vacuo afforded an oil. The oil was separated by flash column chromatography (49:1 hexane/ethyl acetate). The cis-stilbene eluted first as a clear oil followed by the trans isomer as a colorless solid or oil. Overall yield: 91%. To a solution of the trans isomer (3.1.g) in anhydrous dichloromethane (150 mL) at −78° C. was added (dropwise) boron tribromide (1.0 M, 34.5 mL), and the resulting red solution was stirred under argon for 30 min. The solution was poured into water and extracted with dichloromethane. The organic phase was washed with water, and removal of the solvent in vacuo afforded an oil, which was separated by flash column chromatography (1:1 hexane/ethyl acetate) to afford a colorless solid (2.26 g, 86%): mp 260° C.

后处理

  1. stirringthe mixture stirred for 6-15 h
  2. extractionextracted with dichloromethane
  3. washThe organic phase was washed with water, and removal of the solvent in vacuo
  4. customafforded an oil
  5. customThe oil was separated by flash column chromatography (49:1 hexane/ethyl acetate)
  6. washThe cis-stilbene eluted first as a clear oil
  7. additionTo a solution of the trans isomer (3.1.g) in anhydrous dichloromethane (150 mL) at −78° C. was added (dropwise) boron tribromide (1.0 M, 34.5 mL)
  8. stirringthe resulting red solution was stirred under argon for 30 min
  9. additionThe solution was poured into water
  10. extractionextracted with dichloromethane
  11. washThe organic phase was washed with water, and removal of the solvent in vacuo
  12. customafforded an oil, which
  13. customwas separated by flash column chromatography (1:1 hexane/ethyl acetate)

来源与证据

ORD记录
ord-af0b3065524a43a09db516585c6e3e7a
来源数据集
uspto-grants-2012_08
专利号
US08242144B2

关联笔记

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