Sodium hydride → HCID 86759887, compound

HRID 1061593Notes

Reaction equation

HRID 1061593 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]#[C:6][C:7]1[CH:8]=[C:9]([C:13]#[C:14][CH2:15][OH:16])[CH:10]=[CH:11][CH:12]=1.Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].[NH4+].[Cl-]>C1COCC1>[C:19]([CH2:18][O:3][CH2:4][C:5]#[C:6][C:7]1[CH:8]=[C:9]([C:13]#[C:14][CH2:15][O:16][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:10]=[CH:11][CH:12]=1)([OH:21])=[O:20]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 60984Methyl bromoacetateHCID 11435374HCID 11435374, compound

Product 1

HCID 86759887HCID 86759887, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A 60% suspension of NaH (2.1 g, 53.7 mmol) is added to a solution of 3-[3-(3-hydroxyprop-1-ynyl)phenyl]prop-2-yn-1-ol (A5, 0.5 g, 2.68 mmol) in absolute THF (20 ml), and the mixture is stirred at 70° C. for 2 h. After cooling to RT, methyl bromoacetate (5.2 ml, 53.7 mmol) is added dropwise to the reaction solution, and the mixture is stirred at RT overnight. For work-up, the reaction solution is poured into an ice-cooled semisaturated aqueous NH4Cl solution (25 ml) and extracted (2×) with ethyl acetate. The combined organic phases are dried over MgSO4, filtered off and concentrated under reduced pressure. Further purification by chromatography [Tol/Ac (9:1)] over a silica gel column gives the title compound (0.85 g) as a colorless residue. TLC, silica gel, glass plates, [Tol/Ac (7:3)], Rf=0.80.

Workup

  1. temperatureAfter cooling to RT
  2. stirringthe mixture is stirred at RT overnight
  3. temperaturecooled
  4. extractionextracted (2×) with ethyl acetate
  5. dry with materialThe combined organic phases are dried over MgSO4
  6. filtrationfiltered off
  7. concentrationconcentrated under reduced pressure
  8. customFurther purification by chromatography [Tol/Ac (9:1)] over a silica gel column

Sources & evidence

ORD record
ord-755e7aa479cb492e8391d3b5ab01bf0a
Source dataset
uspto-grants-2005_11
Patent number
US06960588B1

Reaction notes

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