Hydrochloric Acid → 127559-62-0

HRID 259991Notes

Reaction equation

HRID 259991 reaction equation
Br[C:2]([CH2:4][CH:5]([OH:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[CH2:3].C[O-].[Na+].Cl>CN1CCCC1=O>[C:7]1([CH2:6][CH:5]([OH:13])[CH2:4][C:2]#[CH:3])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 22404503HCID 22404503, compound

Product 1

HCID 15503593127559-62-0

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

20.00 Grams of the 2-bromo-5-phenyl-1-penten-4-ol obtained above were dissolved in 160 g of N-methyl-2-pyrrolidone, and 11.20 g of sodium methylate were added. The mixture was allowed to react at 30° C. for 14 hours and then was neutralized with concentrated hydrochloric acid. Insolubles were filtered off, and the filtrate was concentrated under reduced pressure. The resultant oily substance was purified by silica gel column chromatography to give 9.96 g of 5-phenyl-1-pentyn-4-ol, nD25 =1.519, FI-MS m/e 160(M+), propargyl compound/allene compound 97.9/2.1.

Workup

  1. customto react at 30° C. for 14 hours
  2. filtrationInsolubles were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resultant oily substance was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7131871c24f848caa35b68d5ac926890
Source dataset
uspto-grants-1996_06
Patent number
US05523495

Reaction notes

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