Benzene, (diazomethyl)- → HCID 18358879, compound

HRID 428441

Reaction equation

HRID 428441 reaction equation
[C:1]1([CH:7]=[N+:8]=[N-:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([OH:25])[C:18]#[C:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:13]([N+:26]([O-:28])=[O:27])[CH:12]=1>C1COCC1>[C:1]1([C:7]2[C:18]([CH:17]([C:14]3[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][C:13]=3[N+:26]([O-:28])=[O:27])[OH:25])=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 136601Benzene, (diazomethyl)-HCID 18358875Ethyl 4-(4-chloro-2-nitrophenyl)-4-hydroxy-2-butynoate

Product 1

HCID 18358879HCID 18358879, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of freshly generated phenyldiazomethane (2.44 g, 20.7 mmol) in 10 mL of anhydrous THF was added to ethyl 4-(4-chloro-2-nitrophenyl)-4-hydroxy-2-butynoate (5.86 g, 20.7 mmol) in 10 mL THF and the mixture was stirred at room temperature for 18 hours. The reaction mixture was quenched with excess ethereal acetic acid and concentrated via rotary evaporation to an oil (12.24 g) which solidified on cooling. This was filtered to yield the title compound as a pale yellow solid (2.42 g). The filtrate was concentrated via rotary evaporation to an oil which was triturated with hexane:ethyl acetate (4:1) to yield an additional 1.52 g of the title compound (48% combined yield).

Workup

  1. customThe reaction mixture was quenched with excess ethereal acetic acid
  2. concentrationconcentrated via rotary evaporation to an oil (12.24 g) which
  3. temperatureon cooling
  4. filtrationThis was filtered

Sources & evidence

ORD record
ord-ebd4aa3b0e114d51a7dcbb6e422f01b2
Source dataset
uspto-grants-2001_11
Patent number
US06313290B1

Linked notes

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