Tetrahydrofuran → HCID 178497701, compound

HRID 1871539Notes

Reaction equation

HRID 1871539 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][CH2:16][C:17]3[C:21](C(OCC)=O)=[CH:20][NH:19][N:18]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.[OH-].[Na+]>O>[CH3:1][OH:6].[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][CH2:16][C:17]3[CH:21]=[CH:20][NH:19][N:18]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178469920HCID 178469920, compound

Product 1

HCID 178497701HCID 178497701, compoundYield 119.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of ethyl 3-[2-(3-cyclopentyloxy-4-methoxyphenyl)ethyl]pyrazole-4-carboxylate (from Example 18), (0.40 g, 1.1 mmol) was stirred overnight with lithium aluminum hydride (0.18 g, 4.7 mmol). THF (25 mL) was added and stirring was continued for 1 hour. The reaction mixture was then treated successively with water (0.2 mL), 15% aqueous sodium hydroxide (0.2 mL) and water (0.6 mL). The inorganic material was filtered and washed and methylene chloride. The organic solutions were combined and evaporated under reduced pressure. The crude product was purified by flash chromatography over 3.5 g of flash chromatography silica gel. Elution with methylene chloride and 1% methanol/methylene chloride removed some impurities. Elution with 2% methanol/methylene chloride gave 0.21 g (60%) of 3-[2-(3-cyclopentyloxy-4-methoxyphenyl)ethyl]pyrazole carbinol. Pure title compound, mp 88-91°, was obtained by crystallization from ether/hexanes.

Workup

  1. filtrationThe inorganic material was filtered
  2. washwashed
  3. customevaporated under reduced pressure
  4. customThe crude product was purified by flash chromatography over 3.5 g of flash chromatography silica gel
  5. washElution with methylene chloride and 1% methanol/methylene chloride
  6. customremoved some impurities
  7. washElution with 2% methanol/methylene chloride

Sources & evidence

ORD record
ord-83b44c95aed747e1a0810f1b1ccd49bd
Source dataset
uspto-grants-2000_08
Patent number
US06103749

Reaction notes

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