2-Methyl-3-butyn-2-ol → HCID 59354761, compound

HRID 1776294Notes

Reaction equation

HRID 1776294 reaction equation
[CH3:1][C:2]([OH:6])([C:4]#[CH:5])[CH3:3].[Li]CCCC.[CH2:12]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]([CH:24]([OH:25])[C:5]#[C:4][C:2]([CH3:3])([OH:6])[CH3:1])=[CH:26][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 82582-Methyl-3-butyn-2-olHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 178418339Butyllithium

Product 1

HCID 59354761HCID 59354761, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a precooled −78° C. solution of 2-methylbut-3-yn-2-ol (4.71 g, 0.05 mol) in THF (250 mL), n-BuLi (51.2 mL, 0.08 mol) was added under an inert atmosphere, and the mixture stirred for 30 min. Then, 4-(benzyloxy)benzaldehyde (8.0 g, 0.037 mol) in THF was added and the mixture was stirred for an additional 3 h at RT, quenched with a saturated NH4Cl solution and concentrated in vacuo. The residue was acidified with HCl (1 N) and extracted with DCM (3×200 mL). The combined organic layers were washed with water, dried over Na2SO4 and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 1-(4-(benzyloxy)phenyl)-4-methylpent-2-yne-1,4-diol (6 g, 54%) as a solid.

Workup

  1. stirringthe mixture was stirred for an additional 3 h at RT
  2. customquenched with a saturated NH4Cl solution
  3. concentrationconcentrated in vacuo
  4. extractionextracted with DCM (3×200 mL)
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto obtain the crude product
  9. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-bcc1ffa6949d423eb0e26f8f68091480
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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