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HRID371445

反应详情

EQUATION

反应方程式

HRID 371445 的结构方程式

REACTANTS

反应物

3
结构：c1c[nH]cn1
HCID795

Imidazole

C3H4N2

结构：CC(C)(C)[Si](C)(C)Cl
HCID28928

Chloro(1,1-dimethylethyl)dimethylsilane

C6H15ClSi

结构：O=C1C[C@@H]2[C@@H](CO)[C@H](OC(=O)c3ccccc3)C[C@@H]2O1
HCID2724454

4-(Hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

C15H16O5

PRODUCTS

生成物

1
结构：CC(C)(C)[Si](C)(C)OC[C@@H]1[C@H]2CC(=O)O[C@H]2C[C@H]1OC(=O)c1ccccc1
HCID2724503

未命名化合物

收率 97.9%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CN(C)C=O
溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

A solution of 11.052 g of (1S,5R,6S,7R)-6-hydroxymethyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one (DOS No. 2,610,718) in 54.0 ml of absolute dimethylformamide is combined with 3.03 g of imidazole and 6.63 g of tert-butyldimethylsilyl chloride, and the mixture is stirred for 3 hours at room temperature. The solution is subsequently precipitated into 500 ml of ice water, the precipitate is suctioned off, and the residue is dissolved in methylene chloride. The organic solution is dried over magnesium sulfate and concentrated. The crude product is recrystallized from hexane, thus obtaining 15.30 g of the title compound, mp 75.8° C.

WORKUP

后处理

  1. customThe solution is subsequently precipitated into 500 ml of ice water
  2. dissolutionthe residue is dissolved in methylene chloride
  3. dry with materialThe organic solution is dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product is recrystallized from hexane