海萝胶 → 4-Benzyloxy-6-[2-(3,4-dibenzyloxyphenyl)-2-hydroxyethyl]-2H-pyran-2-one

HRID 2910

反应方程式

HRID 2910 反应方程式
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([O:20][C:21]1[CH:26]=[C:25]([CH3:27])[O:24][C:23](=[O:28])[CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:29]([O:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][C:44]=1[O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[CH:40]=[O:41])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Cl-].[NH4+].Cl>O1CCCC1>[CH2:13]([O:20][C:21]1[CH:26]=[C:25]([CH2:27][CH:40]([C:39]2[CH:42]=[CH:43][C:44]([O:45][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[C:37]([O:36][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:38]=2)[OH:41])[O:24][C:23](=[O:28])[CH:22]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参与物

8

反应物 6

HCID 313海萝胶HCID 7912二异丙胺HCID 25517氯化铵HCID 795263,4-二苄氧基苯甲醛HCID 27844494-Benzyloxy-6-methyl-2H-pyran-2-oneHCID 178418339正丁基锂

产物 1

HCID 196880744-Benzyloxy-6-[2-(3,4-dibenzyloxyphenyl)-2-hydroxyethyl]-2H-pyran-2-one收率 68%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂3 次

反应条件

温度
-78 °C

实验过程

A solution of 10.1 g (14.0 ml, 100 mmol) diisopropylamine in 150 ml tetrahydrofuran was mixed under nitrogen at -78° C. with 41.0 ml (95 mmol) butyllithium (2.3M in n-hexane). It was allowed to reach 0° C. for a short time and immediately cooled again to -78° C. After a dropwise addition of a solution of 19.0 g (88 mmol) 4-benzyloxy-6-methyl-2H-pyran-2-one (V) in 100 ml anhydrous tetrahydrofuran it was stirred for a further 45 min. at -78° C. and subsequently a solution of 12.8 g (40 mmol) 3,4-dibenzyloxy-benzaldehyde (IV) in 150 ml anhydrous tetrahydro-furan was added dropwise. The internal temperature was gradually increased to -30° C. and it was admixed with an excess of saturated ammonium chloride solution. After acidifying with 6n HCl it was extracted with ethyl acetate, the combined organic phases were dried and evaporated. Purification of the residue by means of flash chromatography on silica gel (mobile solvent: ethyl acetate/heptane 1:2) yielded 14.4 g (68%) VI, melting point 109°-110° C. (ether).

后处理

  1. customto reach 0° C. for a short time
  2. temperatureThe internal temperature was gradually increased to -30° C.
  3. extractionwas extracted with ethyl acetate
  4. customthe combined organic phases were dried
  5. customevaporated
  6. customPurification of the residue by means of flash chromatography on silica gel (mobile solvent: ethyl acetate/heptane 1:2)

来源与证据

ORD记录
ord-e1aa3216ef4c4a1fb552fae720596c8e
来源数据集
uspto-grants-1998_03
专利号
US05731344

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