Benzoyl chloride, 3-nitro- → HCID 19967991, compound

HRID 975961Notes

Reaction equation

HRID 975961 reaction equation
[CH3:1][Si:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][OH:5].[N+:8]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14](Cl)=[O:15])([O-:10])=[O:9]>ClCCCl.C(N(CC)CC)C>[N+:8]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([O:5][CH2:4][CH2:3][Si:2]([CH3:7])([CH3:6])[CH3:1])=[O:15])([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 180132-(Trimethylsilyl)ethanol

Product 1

HCID 19967991HCID 19967991, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
5 °C

Procedure

H--2-Trimethylsilylethyl 3-nitrobenzoate may be prepared as follows: a solution of 41.8 g of 2- trimethylsilylethanol in 200 cm3 of 1,2-dichloroethane and 51 cm3 of triethylamine is added to a solution of 66.0 g of 3-nitrobenzoyl chloride in 1000 cm3 of 1,2-dichloroethane cooled to 5° C. The reaction mixture is stirred for 12 hours at a temperature in the vicinity of 25° C., then the insoluble product is separated by filtration and washed with 2 times 50 cm3 of 1,2-dichloroethane. The filtrate is concentrated to dryness under reduced pressure at 40° C. The oily residue obtained is purified by chromatography on silica [eluent: ethyl acetate/cyclohexane (30/70 by volume)]. The fractions containing the expected product are combined and concentrated to dryness under reduced pressure at 40° C. 76.9 g of 2-trimethylsilylethyl 3-nitrobenzoate are thus obtained in the form of an oil used as it is in subsequent syntheses.

Workup

  1. customH--2-Trimethylsilylethyl 3-nitrobenzoate may be prepared
  2. customthe insoluble product is separated by filtration
  3. washwashed with 2 times 50 cm3 of 1,2-dichloroethane
  4. concentrationThe filtrate is concentrated to dryness under reduced pressure at 40° C
  5. customThe oily residue obtained
  6. customis purified by chromatography on silica [eluent: ethyl acetate/cyclohexane (30/70 by volume)]
  7. additionThe fractions containing the expected product
  8. concentrationconcentrated to dryness under reduced pressure at 40° C

Sources & evidence

ORD record
ord-4c6f67f9998e49539617689e7294db75
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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