Tetrahydrofuran → HCID 57626678, compound

HRID 500084Notes

Reaction equation

HRID 500084 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH:10]([CH:12]([C:14]([O-])=O)O)O)([O-])=O.[Na+].[K+].[C:19]([O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([OH:32])=O)=[CH:25][C:24]=1[O:33][CH3:34])(=[O:21])[CH3:20].O[N:36]1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2N=N1.O1CC[CH2:47][CH2:46]1>ClCCl.C(OCC)(=O)C>[C:19]([O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([NH:36][CH:40]2[CH2:41][CH2:42][CH:43]([CH:7]=[C:10]([CH2:46][CH3:47])[CH2:12][CH3:14])[CH2:44][CH2:39]2)=[O:32])=[CH:25][C:24]=1[O:33][CH3:34])(=[O:21])[CH3:20]

Participants

8

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 757711-HydroxybenzotriazoleHCID 2264844-(Acetyloxy)-3-methoxybenzeneacetic acidHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydride

Product 1

HCID 57626678HCID 57626678, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under nitrogen atmosphere, to a suspension of lithium aluminium hydride (0.76 g) in anhydrous tetrahydrofuran (25 ml) under ice-cooling was added dropwise a solution of the above product (5) (1.3 g) in anhydrous tetrahydrofuran (25 ml), and then the mixture was heated under reflux for 3 hours. To the reaction mixture cooled in an ice-water bath were added dropwise ethyl acetate and 1 M aqueous potassium sodium tartrate to quench an excess of lithium aluminium hydride. The mixture was filtrated through Celite. The filtrate was dried over magnesium sulfate, and then the solvent was removed in vacuo. The mixture of resulting colorless oil (1.1 g, a mixture of cis and trans forms), 4-acetoxy-3-methoxyphenyacetic acid (1.3 g), 1-ethyl-3-(3-dimethyl-aminopropyl)carbodiimide hydrochloride (1.4 g), 1-hydroxybenzotriazole (0.09 g), and dichloromethane (40 ml) was stirred overnight at room temperature. The reaction mixture was washed with water and then brine. The organic layer was dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was purified by a silica gel chromatography (eluent: hexane/ethyl acetate=3/1 to 3/2) to give 1.9 g of 2-(4-acetoxy-3-methoxyphenyl)-N-[4-(2-ethyl-1-butenyl)cyclohexyl]acetamide (1.9 g, a mixture of cis and trans forms).

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. temperatureTo the reaction mixture cooled in an ice-water bath
  5. customto quench an excess of lithium aluminium hydride
  6. filtrationThe mixture was filtrated through Celite
  7. dry with materialThe filtrate was dried over magnesium sulfate
  8. customthe solvent was removed in vacuo
  9. additionThe mixture
  10. customof resulting colorless oil (1.1 g
  11. washThe reaction mixture was washed with water
  12. dry with materialThe organic layer was dried over magnesium sulfate
  13. customthe solvent was removed in vacuo
  14. customThe residue was purified by a silica gel chromatography (eluent: hexane/ethyl acetate=3/1 to 3/2)

Sources & evidence

ORD record
ord-12a0cd8ab8c34e1ca0c44ed5bf591414
Source dataset
uspto-grants-2010_08
Patent number
US07767854B2

Reaction notes

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