Bromotrimethylsilane → HCID 21458725, compound

HRID 725606Notes

Reaction equation

HRID 725606 reaction equation
C[Si]([Br:5])(C)C.[CH2:6]([O:13][C:14]1[C:23]2[O:22][CH2:21][CH2:20][O:19][C:18]=2[CH:17]=[C:16]([CH2:24]O)[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)(Cl)Cl>[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([CH:17]=[C:18]2[O:19][CH2:20][CH2:21][O:22][C:23]=12)[CH2:24][Br:5])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 21458738HCID 21458738, compound

Product 1

HCID 21458725HCID 21458725, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.07 ml of trimethylsilyl bromide is added to a solution of 0.1 g of 5-benzyloxy-7-hydroxymethyl-1,4-benzodioxane in 5 ml of chloroform and the mixture is stirred for a further 15 minutes at room temperature and then concentrated by evaporation in a rotary evaporator. The residue is immediately dissolved in a small amount of ethyl acetate; the same volume of hexane is added and the mixture is filtered through 15 g of silica gel, followed by elution with a mixture (hexane/ethyl acetate=4:1). Concentration of the eluates by evaporation yields the title compound: Rf (hexane/ethyl acetate: 3:1)=0.48.

Workup

  1. concentrationconcentrated by evaporation in a rotary evaporator
  2. dissolutionThe residue is immediately dissolved in a small amount of ethyl acetate
  3. additionthe same volume of hexane is added
  4. filtrationthe mixture is filtered through 15 g of silica gel
  5. washfollowed by elution with a mixture (hexane/ethyl acetate=4:1)
  6. customConcentration of the eluates by evaporation

Sources & evidence

ORD record
ord-e26b07c7c78c4f5bb3f49193ea771a22
Source dataset
uspto-grants-1998_01
Patent number
US05705658

Reaction notes

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