Potassium hydride → (2-Naphthyl)propyl tributylstannylmethyl ether

HRID 654960Notes

Reaction equation

HRID 654960 reaction equation
[H-].[K+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][CH2:14][CH2:15][OH:16].[CH2:17]([Sn:21]([CH2:30]I)([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH3:20]>O1CCCC1.CCCCCC>[CH2:17]([Sn:21]([CH2:30][O:16][CH2:15][CH2:14][CH2:13][C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:3]=1)([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:26][CH2:27][CH2:28][CH3:29])[CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 3

HCID 82127Potassium hydrideHCID 10862926Tributyl(iodomethyl)stannaneHCID 112062322-Naphthalenepropanol

Product 1

HCID 67916977(2-Naphthyl)propyl tributylstannylmethyl ether

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Potassium hydride (315 mg, 7.87 mmol) was added to a solution of 3-(2-naphthyl)propan-1-ol (1.33 g, 7.16 mmol) in tetrahydrofuran (10 ml) at room temperature under argon. After 1/2 hour, a solution of tributylstannylmethyliodide (3.09 g, 7.16 mmol) in tetrahydrofuran (2 ml) was added. After stirring at room temperature for 10 days, the mixture was diluted with hexane and washed thoroughly with water. Evaporation of the dried (magnesium sulphate) organic layer gave an oil, which was flash chromatographed on silica using 5% ethyl ether/petroleum ether. The title ether was obtained as a colorless oil.

Workup

  1. washwashed thoroughly with water
  2. customEvaporation of the
  3. dry with materialdried (magnesium sulphate) organic layer
  4. customgave an oil, which
  5. customchromatographed on silica using 5% ethyl ether/petroleum ether
  6. customThe title ether was obtained as a colorless oil

Sources & evidence

ORD record
ord-d423e84c4e314bef914234b9b4310691
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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