Ammonium Chloride → HCID 67050087, compound

HRID 2103797Notes

Reaction equation

HRID 2103797 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:18][CH:19]=[C:20]([C:26](OCC)=[O:27])[C:21]=2[O:22][CH2:23][O:24][CH3:25])=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8].[Cl-].[NH4+]>C1COCC1>[C:7]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:18][CH:19]=[C:20]([CH2:26][OH:27])[C:21]=2[O:22][CH2:23][O:24][CH3:25])=[CH:13][CH:12]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 670503162-(4-t-Butylphenyl)-3-methoxymethyloxy-4-ethoxycarbonylthiophene

Product 1

HCID 67050087HCID 67050087, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To lithium aluminium hydride (27 mg, 0.72 mmol) in THF (0.86 mL), 2-(4-t-butylphenyl)-3-methoxymethyloxy-4-ethoxycarbonylthiophene (0.21 g, 0.60 mmol) in THF (0.86 mL) was added dropwise under cooling with ice, and the reaction solution was stirred under cooling with ice for 1 hour. After addition of saturated aqueous ammonium chloride, the reaction solution was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1) to give the desired product as a colorless oil (87 mg, yield 47%).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice for 1 hour
  3. extractionthe reaction solution was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-5a3f02df7a5444d7b8587641d0a6f204
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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