Water → HCID 22324922, compound

HRID 496424Notes

Reaction equation

HRID 496424 reaction equation
[CH3:1][C:2]([O:9][C:10]1[CH:19]=[CH:18][C:17]2[C:16](=[O:20])[CH2:15][CH2:14][CH2:13][C:12]=2[C:11]=1[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:8])[C:3](OCC)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.CCOCC>[OH:4][CH2:3][C:2]([CH3:8])([CH3:1])[O:9][C:10]1[C:11]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]([OH:20])[CH2:15][CH2:14][CH2:13]2

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22324896HCID 22324896, compound

Product 1

HCID 22324922HCID 22324922, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 2-methyl-2-{[5-oxo-1-(2-phenylethyl)-5,6,7,8-tetrahydro-2-naphthalenyl]oxy}propanoate (1.00 g, 2.62 mmol) in tetrahydrofuran (4 mL) was added to an ice-cooled suspension of lithium aluminum hydride (150 mg, 3.94 mmol) in tetrahydrofuran (1 mL) the mixture was stirred at room temperature for 1 h, and was then cooled in ice and treated sequentially with water (0.15 mL), 15% aqueous sodium hydroxide (0.15 mL) and water (0.45 mL). The mixture was stirred at room temperature for 10 min, and was then diluted with ether (5 mL) and filtered. The filtrate was concentrated to give 6-(2-hydroxy-1,1-dimethylethoxy)-5-(2-phenylethyl)-1,2,3,4-tetrahydro-1-naphthalenol as a white solid, 0.856 g, 95% yield. NMR spectrum was consistent with structure. Calcd. for C22H28O3: Theory: C, 77.61; H, 8.29. Found: C, 77.42; H, 8.34. 3. 6-(2-Hydroxy-1,1-dimethylethoxy)-5-(2-phenylethyl)-3,4-dihydro-1(2H)-naphthalenone

Workup

  1. temperaturecooled
  2. temperaturewas then cooled in ice
  3. stirringThe mixture was stirred at room temperature for 10 min
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-41a10dd19ecc49c18639dc4ccc9d61ba
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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