3-Methoxypropyne → HCID 178495081, compound

HRID 1631438Notes

Reaction equation

HRID 1631438 reaction equation
[CH3:1][O:2][CH2:3][C:4]#[CH:5].[Li]CCCC.[CH2:11]([N:18]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C@H:19]1[CH2:24][CH2:23][C@H:22]([C:25](N(OC)C)=[O:26])[CH2:21][CH2:20]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[CH2:31]([N:18]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C@H:19]1[CH2:20][CH2:21][C@H:22]([C:25](=[O:26])[C:5]#[C:4][CH2:3][O:2][CH3:1])[CH2:23][CH2:24]1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 693933-MethoxypropyneHCID 178418339ButyllithiumHCID 178502725HCID 178502725, compound

Product 1

HCID 178495081HCID 178495081, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of 3-methoxyprop-1-yne (0.207 ml, 2.456 mmol) in THF (2 mL) was treated with BuLi (1.535 ml, 2.456 mmol) dropwise at −78° C. After stirring for 15 min, 13D (300 mg, 0.819 mmol) in THF (2 mL) was added and reaction mixture was warmed to room temperature over 30 min. The reaction was quenched with aq. HOAc and extracted with ethyl acetate (3×). The combined organics were washed with brine, dried over anhydrous magnesium sulphate and concentrated under reduced pressure. The residue was purified by Isco silica column (12 g), eluted with ethyl acetate:hexane, 0-70%. Concentration of the appropriate fractions provided 13E (300 mg, 98% yield). This material was taken without characterization to the next step.

Workup

  1. customreaction mixture
  2. customThe reaction was quenched with aq. HOAc
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by Isco silica column (12 g)
  8. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-29bea5378e404c828f3110b97a0777ae
Source dataset
uspto-grants-2014_07
Patent number
US08791257B2

Reaction notes

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