Hexane → HCID 18647278, compound

HRID 345232Notes

Reaction equation

HRID 345232 reaction equation
Br[C:2](Br)=[CH:3][C@@H:4]([O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)[C@@:5]([O:11][CH3:12])([CH3:10])[CH2:6][CH2:7][CH2:8][CH3:9].[Mg].CCCCCC>C1COCC1>[O:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH:14]1[O:13][C@@H:4]([C@@:5]([O:11][CH3:12])([CH3:10])[CH2:6][CH2:7][CH2:8][CH3:9])[C:3]#[CH:2]

Participants

5

Reactant 3

HCID 8058HexaneHCID 5462224MagnesiumHCID 18647280HCID 18647280, compound

Product 1

HCID 18647278HCID 18647278, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (3R,4R)l,l-dibromo-3-tetrahydro-pyranyloxy-4-methoxy-4-methyl-l-octene (240 mg; 0.58 mmol) in THF (2 ml) is added dropwise to a refluxing mixture of activated magnesium turnings (activated with I2, 183 mg, 0.75 mmol) in THF (1 ml). The mixture is refluxed for 1 h, hexane (5 ml) is added and the suspension is filtered through a short path of silica gel. The filter cake is washed with ether and the solvent is removed in vacuo. The alkyne (3R,4R)3-tetrahydropyranyloxy-4-methoxy-4-methyl-l-octyne is purified by column chromatography on silica gel, eluting with 5% EtOAc in petroleum ether, to afford (3R,4R)3-tetrahydropyranyloxy-4-methoxy-4-methyl-l-octyne.

Workup

  1. temperatureThe mixture is refluxed for 1 h
  2. filtrationthe suspension is filtered through a short path of silica gel
  3. washThe filter cake is washed with ether
  4. customthe solvent is removed in vacuo
  5. customThe alkyne (3R,4R)3-tetrahydropyranyloxy-4-methoxy-4-methyl-l-octyne is purified by column chromatography on silica gel
  6. washeluting with 5% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-3235149a4aca4ff2907bfc01f3b17aa0
Source dataset
uspto-grants-1991_10
Patent number
US05055592

Reaction notes

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