HRID1925238

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID244

Benzyl alcohol

C7H8O

HCID8471

Triethylamine

C6H15N

HCID85557

6-Hydroxy-2-naphthoic acid

C11H8O3

结构：CC(=O)OCC1=C[C@H]2[C@@H]3C(C)(C)[C@]3(OC(=O)Cc3ccccc3)C[C@@H](C)[C@]2(O)[C@@H]2C=C(C)C(=O)[C@@]2(O)C1

HCID3034821

3-[(Acetyloxy)methyl]-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9aH-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl phenylacetate

C30H36O7

PRODUCTS

生成物

HCID67520229

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID1140

Toluene

C7H8

PROCEDURE

实验过程

6-Hydroxy-2-naphthoic acid (30 g, 160 mmol, Aldrich), dppa (48.4 g, 176 mmol, Aldrich), benzyl alcohol (51.8 g, 480 mmol, Aldrich) and Et3N (32.3 g, 320 mmol, Aldrich) were heated at reflux with toluene (500 mL, Aldrich) for 16 h. After cooling to RT, the volatile portion was removed in vacuo. The resulting brown residue was purified by silica gel column chromatography (40% EtOAc/hexane) to give crude compound, which was further purified by crystallization from 50% EtOAc/Hexane to give the title compound as an off-white solid. MS (ESI, pos. ion) m/z: 294.2 (M+1). Mass Calc'd for C18H15NO3: 293.11.

WORKUP

后处理

customthe volatile portion was removed in vacuo
customThe resulting brown residue was purified by silica gel column chromatography (40% EtOAc/hexane)
customto give crude compound, which
customwas further purified by crystallization from 50% EtOAc/Hexane