Isobutanol → HCID 22717712, compound

HRID 1582561Notes

Reaction equation

HRID 1582561 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[NH:13][C:12](=[O:14])[O:11][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][CH:16]([CH3:19])[CH2:17]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:15][CH:16]([CH3:19])[CH2:17][N:13]1[C:12](=[O:14])[O:11][N:10]=[C:9]1[O:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6560IsobutanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 13574419151991-60-7

Product 1

HCID 22717712HCID 22717712, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A 50 mL round bottom flask equipped with a thermometer, a stirrer, addition funnel and nitrogen inlet was charged with 3-(phenylmethoxy)-1,2,4-oxadiazol-5(4H)-one (1 g, 5.2 mmol), 2-methyl propanol (0.45 g, 6 mmol), triphenylphosphine (1.57 g, 6 mmol) and tetrahydrofuran (5 mL). The mixture was cooled to 0° C. and a solution of diethyl azodicarboxylate (1.04 g, 6 mmol) in tetrahydrofuran (2 mL) was added dropwise over a period of 10 min. The reaction mixture was allowed to warm to room temperature, and stirred for 18 h. The entire mixture was flash chromatographed (silica gel, 8:2 hexane-ethyl acetate) to provide 1.1 g (84%) of the title compound as a white solid melting at 53-60° C.

Workup

  1. customA 50 mL round bottom flask equipped with a thermometer, a stirrer, addition funnel and nitrogen inlet
  2. temperatureto warm to room temperature
  3. customchromatographed (silica gel, 8:2 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-6dc21c0d8b05440a88d4afef33b44ac3
Source dataset
uspto-grants-2004_05
Patent number
US06737383B1

Reaction notes

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