Ethyl Acetate → HCID 19013937, compound

HRID 1728516Notes

Reaction equation

HRID 1728516 reaction equation
[CH3:1][C@@H:2]([C@@H:5]([O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1)[CH3:6])[CH2:3][OH:4].[CH2:14](I)[CH2:15][CH2:16][CH3:17].[H-].[Na+].C(OCC)(=O)C>CN(C=O)C>[CH2:14]([O:4][CH2:3][CH:2]([CH3:1])[CH:5]([O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1)[CH3:6])[CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 11194794HCID 11194794, compound

Product 1

HCID 19013937HCID 19013937, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.88 g (10 retool) of the crude (2R,3S)-2-methyl-3-tetrahydropyranyloxy-l-butanol was dissolved in 30 ml of DMF. Thereto was added 18.4 g of n-BuI. Thereto was further added carefully by small portions 4 g of oily sodium hydride (about 60%), with ice cooling. To the reaction mixture was added 300 ml of ethyl acetate. The insoluble materials were removed by filtration. The filtrate was washed with two 100 ml-portions of water, dried and concentrated under reduced pressure to obtain crude 1-butoxy-2-methyl-3-tetrahydropyranyloxybutane as an oily material. This crude product was dissolved in 150 ml of methanol. 5 g of Amberlist 15 was added thereto, and the mixture was stirred for 2 days at room temperature. The Amberlist 15 was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was subjected to Kugelrohr distillation to obtain 0.90 g of the title compound as an oily material.

Workup

  1. customThe insoluble materials were removed by filtration
  2. washThe filtrate was washed with two 100 ml-portions of water
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-442cf00a46cc4733a64ddb15477b631a
Source dataset
uspto-grants-1994_07
Patent number
US05328643

Reaction notes

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