3-甲氧基-4-羟基肉桂酸 → 3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid 4-bromobutyl ester

HRID 456382

反应方程式

HRID 456382 反应方程式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[O:13][CH3:14].[CH2:15]1[CH2:19]O[CH2:17][CH2:16]1.C(Br)(Br)(Br)[Br:21]>>[Br:21][CH2:17][CH2:16][CH2:15][CH2:19][O:11][C:10](=[O:12])[CH:9]=[CH:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([O:13][CH3:14])[CH:4]=1

参与物

4

反应物 3

HCID 7093-甲氧基-4-羟基肉桂酸HCID 8028四氢呋喃HCID 11205四溴化碳

产物 1

HCID 539389163-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid 4-bromobutyl ester收率 265.4%

实验过程

To a solution of 3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid (10 g, 51.5 mmoles) in THF (400 ml) triphenylphosphine (2.7 g, 10.3 mmoles) and carbon tetrabromide (34.16 g, 10.3 mmoles) are added and the solution is left at room temperature, under magnetic stirring, for 48 hours. The solid is filtered and then evaporated at reduced pressure. The obtained crude product is purified by chromatogrphy on silica gel eluting with n-hexane/ethyl acetate 7/3. 9 g of 3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid 4-bromobutyl ester are obtained. M.p.=86–89° C.

后处理

  1. filtrationThe solid is filtered
  2. customevaporated at reduced pressure
  3. customThe obtained crude product
  4. customis purified by chromatogrphy on silica gel eluting with n-hexane/ethyl acetate 7/3

来源与证据

ORD记录
ord-33a64039ad28475ca8609752b4369940
来源数据集
uspto-grants-2007_03
专利号
US07186708B2

关联笔记

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