Ammonium Chloride → HCID 11429505, compound

HRID 2120469Notes

Reaction equation

HRID 2120469 reaction equation
[CH2:1]([C:3]([OH:33])([CH2:31][CH3:32])[CH2:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:10]=[C:11]([CH:28]=[CH:29][CH:30]=1)[O:12][CH2:13][C:14]1[CH:15]=[C:16]([C:24](OC)=[O:25])[C:17](=[CH:22][CH:23]=1)[C:18](OC)=[O:19])[CH3:8])[CH3:2].[BH4-].[Li+].[Cl-].[NH4+]>C1COCC1>[OH:25][CH2:24][C:16]1[CH:15]=[C:14]([CH:23]=[CH:22][C:17]=1[CH2:18][OH:19])[CH2:13][O:12][C:11]1[CH:10]=[C:9]([CH:7]([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]([CH2:1][CH3:2])([OH:33])[CH2:31][CH3:32])[CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 23439954HCID 23439954, compound

Product 1

HCID 11429505HCID 11429505, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

220 mg (0.48 mmol) of dimethyl 4-[3-(5-ethyl-5-hydroxy-1-methylheptyl)phenoxymethyl]phthalate are dissolved in 15 ml of anhydrous THF. 42 mg (1.9 mmol) of lithium borohydride are then added and the reaction medium is heated under reflux for 12 hours. After cooling, treating with a saturated ammonium chloride solution and extracting with ethyl acetate, the organic phase is dried and concentrated under reduced pressure. The residue is then purified by chromatography on a silica column. A colourless oil is obtained (m=132 mg; Y=75%).

Workup

  1. temperaturethe reaction medium is heated
  2. temperatureunder reflux for 12 hours
  3. temperatureAfter cooling
  4. extractionextracting with ethyl acetate
  5. customthe organic phase is dried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is then purified by chromatography on a silica column
  8. customA colourless oil is obtained (m=132 mg; Y=75%)

Sources & evidence

ORD record
ord-287bddc825db456aba0858708287ffc3
Source dataset
uspto-grants-2004_02
Patent number
US06689922B1

Reaction notes

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