HCID 18357646, compound → HCID 18357488, compound

HRID 428055Notes

Reaction equation

HRID 428055 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][CH:17]=[O:18])=[N:2]1.[CH2:19]([Mg]Br)[CH:20]=[CH2:21]>O1CCCC1.C(OCC)C>[OH:18][CH:17]([CH2:21][CH:20]=[CH2:19])[CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1][N:2]=1

Participants

5

Reactant 2

HCID 18357646HCID 18357646, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 18357488HCID 18357488, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2 g of 2-[2-(1,2-benzisoxazol-3-yl)-phenyl]acetaldehyde in 50 ml of tetrahydrofuran at −78° C. under a nitrogen atmosphere was added 10 ml of a 1 M solution of allyl magnesium bromide in diethyl ether. The solution was warmed to room temperature and stirred for a further 2 h then quenched by addition of 50 ml of saturated aqueous ammonium chloride. The aqueous layer was extracted with 150 ml then 100 ml of dichloromethane and the combined organic extracts dried over sodium sulfate and evaporated to give crude product which was purified by chromatography eluting with 20% ethyl acetate in hexane, affording 1 g of 3-[2-(2-Hydroxy-4-pentenyl)phenyl]-1,2-benzisoxazole, 1H-NMR (200 MHz, CDCl3) d 5.8 (CH═CH2).

Workup

  1. customthen quenched by addition of 50 ml of saturated aqueous ammonium chloride
  2. extractionThe aqueous layer was extracted with 150 ml
  3. dry with material100 ml of dichloromethane and the combined organic extracts dried over sodium sulfate
  4. customevaporated
  5. customto give crude product which
  6. customwas purified by chromatography
  7. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-677e87a08c84471ea35ddd7c72c4bfe1
Source dataset
uspto-grants-2001_11
Patent number
US06313139B1

Reaction notes

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