Neopentyl alcohol → HCID 86748268, compound

HRID 2380272Notes

Reaction equation

HRID 2380272 reaction equation
[CH:1]([O:4][N:5]=[C:6]([N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9](O)[CH:8]=1)([CH3:3])[CH3:2].[CH3:19][C:20]([CH3:24])(C)[CH2:21]O.[C:25]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH:1]([O:4][N:5]=[C:6]([N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:25][CH2:21][CH:20]([CH3:24])[CH3:19])[CH:8]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6404Neopentyl alcoholHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 85664898HCID 85664898, compound

Product 1

HCID 86748268HCID 86748268, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

2.5 g (0. 010M) of 1-(O-isopropyl-3-hydroxybenzohydroximoyl)-1H-1,2,4-triazole of, 0.9 g (10.0 mmol) of 2,2-dimethyl-1-propanol, and 2.6 g (10.0 mmol) of triphenylphosphine were dissolved in 40 ml of tetrahydrofuran. The solution was cooled to not more than 10° C. in a water bath. To the solution was added 1.7 g (10.0 mmol) of diethyl azodicarboxylate drop by drop so that the temperature of the solution was not over 20° C. The mixture was stirred overnight, and then heated to 60° C. The reaction mixture was then concentrated. The residue was purified by column chromatography, thus obtaining 0.8 g (yield: 25%) of the desired product having a refractive index of [nD20 ] 1.5202 at 20° C.

Workup

  1. temperatureThe solution was cooled to not more than 10° C. in a water bath
  2. customwas not over 20° C
  3. concentrationThe reaction mixture was then concentrated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4b06179de85b4c8fa8697afaf5684107
Source dataset
uspto-grants-1994_11
Patent number
US05366988

Reaction notes

Loading…