Hydrochloric Acid → HCID 19981147, compound

HRID 1460907Notes

Reaction equation

HRID 1460907 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[Cl:5][C:6]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:7]=1[O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:14](=[O:15])[O:13][C:12]2([CH2:20][CH3:21])O.Cl>O1CCCC1>[Cl:5][C:6]1[CH:25]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:23]=[CH:22][C:7]=1[O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:14](=[O:15])[O:13][C:12]2([CH2:20][CH3:21])[CH:1]=[CH2:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 19799668HCID 19799668, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 19981147HCID 19981147, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 1M solution of vinyl magnesium bromide in tetrahydrofuran (46 ml) was added dropwise at 25° C. a solution of 5-(2'-chloro-4'trifluoromethylphenoxy)-3-ethyl-3-hydroxy- phthalide (2.3 g) in dry tetrahydrofuran (25 ml). After the addition was complete, the solution was stirred for 1 hour and poured into a mixture of ice and concentrated hydrochloric acid. The mixture was stirred for one hour, extracted with methylene chloride, washed with water and dried with sodium sulphate. Chromatography on silica with methylene chloride as eluant yielded a pale orange oil later obtained as colorless crystals (mp. 77°-79° C.).

Workup

  1. additionAfter the addition
  2. stirringThe mixture was stirred for one hour
  3. extractionextracted with methylene chloride
  4. washwashed with water
  5. dry with materialdried with sodium sulphate
  6. customChromatography on silica with methylene chloride as eluant yielded a pale orange oil

Sources & evidence

ORD record
ord-c980fc780c0a4a19878ad6e17aeeae52
Source dataset
uspto-grants-1991_12
Patent number
US05073192

Reaction notes

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