Allyl Alcohol → [3-(5-Bromothien-2-yl)-4,5-dihydroisoxazol-5-yl]methanol

HRID 747196Notes

Reaction equation

HRID 747196 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH:7]=[N:8][OH:9])=[CH:4][CH:3]=1.[CH2:10]([OH:13])[CH:11]=[CH2:12]>O1CCCC1>[Br:1][C:2]1[S:6][C:5]([C:7]2[CH2:12][CH:11]([CH2:10][OH:13])[O:9][N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7858Allyl AlcoholHCID 200491N-[(5-bromothiophen-2-yl)methylidene]hydroxylamine

Product 1

HCID 17954475[3-(5-Bromothien-2-yl)-4,5-dihydroisoxazol-5-yl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-thiophene-2-carbaldehyde oxime (40.2 g, 195.2 mmol) and allyl alcohol (32.4 ml) were added to tetrahydrofuran (200 ml) and then bleach (1318 ml) was added. The reaction was stirred for four hours followed by extraction with tetrahydrofuran (2×200 ml). The organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give the desired product (19 g).

Workup

  1. additionwas added
  2. extractionfollowed by extraction with tetrahydrofuran (2×200 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-559ae188f9b84d10bd02bb3c32e997cc
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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