Sodium hydride → 1-(3-Propoxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)ethanone

HRID 1883266Notes

Reaction equation

HRID 1883266 reaction equation
[OH:1][C:2]1[C:3]([C:16](=[O:18])[CH3:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[H-].[Na+].[CH2:21](I)[CH2:22][CH3:23]>CN(C=O)C>[CH3:13][C:9]1([CH3:12])[CH2:8][CH2:7][C:6]([CH3:15])([CH3:14])[C:5]2[CH:4]=[C:3]([C:16](=[O:18])[CH3:17])[C:2]([O:1][CH2:21][CH2:22][CH3:23])=[CH:11][C:10]1=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 2266995,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl methyl ketone2×

Product 1

HCID 101494431-(3-Propoxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (Intermediate 4, 6.4 g, 26 mmol) in DMF (100 mL) at 0° C. was added NaH (1.2 g, 60%, 31 mmol). After stirring for 30 min, PrI (3.0 mL, 31 mmol) was added. The reaction was stirred at 0° C. for 4 h, was quenched with aqueous NH4Cl and extracted with Et2O (×2). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo.

Workup

  1. stirringThe reaction was stirred at 0° C. for 4 h
  2. customwas quenched with aqueous NH4Cl
  3. extractionextracted with Et2O (×2)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-219f04e671c14196a0b3412061531b15
Source dataset
uspto-grants-2004_07
Patent number
US06759547B1

Reaction notes

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