Pyripropanol → HCID 19885998, compound

HRID 654965Notes

Reaction equation

HRID 654965 reaction equation
[H-].[K+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][OH:12].[CH2:13]([Sn:17]([CH2:26]I)([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16]>O1CCCC1.CCOCC>[CH2:13]([Sn:17]([CH2:26][O:12][CH2:11][CH2:10][CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1)([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 72922PyripropanolHCID 82127Potassium hydrideHCID 10862926Tributyl(iodomethyl)stannane

Product 1

HCID 19885998HCID 19885998, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium hydride (52 mg, 1.30 mmol) was added to a solution of 3-(2-pyridyl)propan-1-ol (161.8 mg, 1.18 mmol) in tetrahydrofuran (3 ml) at room temperature under argon. After 30 minutes, a solution of tributylstannylmethyl iodide (510 mg, 1.18 mmol) in tetrahydrofuran (0.5 ml) was added. After stirring was continued at room temperature for 9 days, the mixture was diluted with ether and washed thoroughly with water. Evaporation of the dried (magnesium sulphate) organic layer gave an oil, which was flash chromatographed on silica using 60% ethyl ether/hexane. Fractions with Rf of about 0.53 on evaporation gave the title ether as a bright yellow oil.

Workup

  1. waitwas continued at room temperature for 9 days
  2. washwashed thoroughly with water
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulphate) organic layer
  5. customgave an oil, which
  6. customchromatographed on silica using 60% ethyl ether/hexane
  7. customFractions with Rf of about 0.53 on evaporation
  8. customgave the title ether as a bright yellow oil

Sources & evidence

ORD record
ord-e0f89602aa1449f88d4fe1f4f12d2ac0
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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