Acetic Anhydride → Lithium Hexamethyldisilazide

HRID 72058Notes

Reaction equation

HRID 72058 reaction equation
[CH3:1][Si:2]([NH-:5])([CH3:4])[CH3:3].[CH3:6][Si:7]([NH-])([CH3:9])[CH3:8].[Li+:11].[Li+].COC1[C@@H](O)[C@@H]2[C@@]3(N(CCC4C2=CC2OCOC=2C=4)CCC3)C=1.C(OC(=O)C)(=O)C>O1CCCC1.C([Li])CCC>[CH3:1][Si:2]([N-:5][Si:7]([CH3:9])([CH3:8])[CH3:6])([CH3:4])[CH3:3].[Li+:11]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 65305CephalotaxineHCID 86588160Lithim bis(trimethylsilylamide)

Product 1

HCID 2733832Lithium Hexamethyldisilazide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 178418339ButyllithiumSolvent

Procedure

A commercial solution of lithium bis-(trimethylsilylamide) 1M in tetrahydrofurane (0.95 ml, 0.95 mmol) was added to a stirred solution of (−)-cephalotaxine (200 mg, 0.63 mmol) in anhydrous tetrahydrofurane at −40° C. After stirring for 5 minutes, acetic anhydride (90 μl, 0.95 mmol) was added, and the reaction mixture was treated like method above-mentioned in 1°). The product thus obtained showed identical characteristics to this obtained above in butyllithium method.

Workup

  1. additionthe reaction mixture was treated like method above-mentioned in 1°)
  2. customThe product thus obtained

Sources & evidence

ORD record
ord-bc16601f6b66472e9f5fd113ba975952
Source dataset
uspto-grants-2014_09
Patent number
USRE045128E1

Reaction notes

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