Allyl Alcohol → [3-(4-Bromophenyl)-4,5-dihydro-1,2-oxazol-5-yl]methanol

HRID 747181Notes

Reaction equation

HRID 747181 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]=[N:7][OH:8])=[CH:4][CH:3]=1.[CH2:11]([OH:14])[CH:12]=[CH2:13]>O1CCCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[CH2:13][CH:12]([CH2:11][OH:14])[O:8][N:7]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7858Allyl AlcoholHCID 6080884-Bromobenzaldehyde Oxime

Product 1

HCID 15888252[3-(4-Bromophenyl)-4,5-dihydro-1,2-oxazol-5-yl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Bromo-benzaldehyde oxime (162 g, 789.9 mmol) and allyl alcohol (130.5 ml) were added to tetrahydrofuran (1000 ml) and then bleach (5305 ml) was added. The reaction was cooled to 0° C. and stirred for 3 hrs. The precipitate was collected and washed with water (2×300 ml) to give the desired product (137 g).

Workup

  1. additionwas added
  2. customThe precipitate was collected
  3. washwashed with water (2×300 ml)

Sources & evidence

ORD record
ord-e016b6fdce5d44569339c050c2dfa5ea
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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