Neopentyl alcohol → HCID 21062968, compound

HRID 1242867Notes

Reaction equation

HRID 1242867 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([OH:11])[N:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:7]=1)=[O:5])[CH3:2].[CH2:18](O)[C:19]([CH3:22])([CH3:21])[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([O:11][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[N:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6404Neopentyl alcoholHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178472659HCID 178472659, compound

Product 1

HCID 21062968HCID 21062968, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold mixture of 50 mg (0.21 mmol) of 1-Ethoxycarbonylmethyl-5-hydroxy-1H-pyrazole-3-carboxylic acid ethyl ester in 2 mL of tetrahydrofuran was added 49 mg (0.25 mmol) of neopentyl alcohol, 108 mg (0.41 mmol) of triphenylphosphine, followed by 0.081 mL (0.41 mmol) of diisopropyl azodicarboxylate (DIAD) and the mixture was allowed to warm up to rt and stirred at rt overnight. The reaction mixture was then concentrated and the residue was chromatographed on silica gel (3:1 hexane:ethyl acetate) to give 46 mg (70%) of 5-(2,2-dimethyl-propoxy)-1-ethoxycarbonylmethyl-1H-pyrazole-3-carboxylic acid ethyl ester LC-MS calcd. for C15H24N2O5 [M++H]: 313.2; found: 313.2.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customthe residue was chromatographed on silica gel (3:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-7f3f6d7781cf4076be5bfac006ecf94f
Source dataset
uspto-grants-2006_10
Patent number
US07115749B2

Reaction notes

Loading…