Water → HCID 20191014, compound

HRID 2119126Notes

Reaction equation

HRID 2119126 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][CH2:12][O:13][C:14]([CH3:16])=[O:15].[N+:17]([C:20]1[CH:24]=[CH:23][N:22]([CH2:25][CH2:26][CH:27]=[O:28])[N:21]=1)([O-:19])=[O:18].O>C1COCC1>[OH:28][CH:27]([CH2:26][CH2:25][N:22]1[CH:23]=[CH:24][C:20]([N+:17]([O-:19])=[O:18])=[N:21]1)[CH2:16][C:14]([O:13][CH2:12][CH3:11])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2733832Lithium HexamethyldisilazideHCID 201910113-Nitro-1H-pyrazole-1-propanal

Product 1

HCID 20191014HCID 20191014, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium bis(trimethylsilyl)amide (10 ml. of a 1M solution in THF) was cooled to -75° under argon and freshly distilled EtOAc (0.88 g.) was added over 5 minutes. Crude 3-(3-nitropyrazol-1-yl)propionaldehyde (1.75 g.) in dry THF (10 ml.) was added at -75° over 10 minutes and the mixture was kept at -75° for a further 15 minutes then allowed to warm to 20° . Water (200 ml.) was added and the mixture was extracted with EtOAc (3×60 ml.). The extracts were dried (MgSO4) and evaporated in vacuo to give crude ethyl 3-hydroxy-5-(3-nitropyrazol-1-yl)valerate as an oil (2.41 g.) which was used in the next stage without further purification. The n.m.r. spectrum in CD3OD included the following resonances: 7.76 (d, 1H): 6.86 (d, 1H); 4.36 (t, 2H); 4.1 (q, 2H); 3.9 (m, 1H); 2.47 (d, 2H); 2.1 (m, 2H); 1.24 (t, 3H).

Workup

  1. temperatureto warm to 20°
  2. extractionthe mixture was extracted with EtOAc (3×60 ml.)
  3. dry with materialThe extracts were dried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-1b86e31c3c3949d39a7d50806ab0ef07
Source dataset
uspto-grants-1987_07
Patent number
US04683228

Reaction notes

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