Methanol → HCID 21278525, compound

HRID 2291919Notes

Reaction equation

HRID 2291919 reaction equation
[CH2:1]([N:4]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5]1)[C:2]#[CH:3].CO.[C-:13]#[N:14].[Na+]>[C-]#N.[Na+].O.C(O)(=O)C>[OH:10][CH:9]([C:6]1[CH:7]=[CH:8][N:4]([CH2:1][C:2]#[CH:3])[CH:5]=1)[C:13]#[N:14]

Participants

7

Reactant 3

HCID 887MethanolHCID 8929Sodium CyanideHCID 13604946[1-(Prop-2-yn-1-yl)-1H-pyrrol-3-yl]methanol

Product 1

HCID 21278525HCID 21278525, compoundYield 97.6%

Reagents, catalysts & solvents 3

HCID 8929Sodium CyanideCatalystHCID 176Acetic AcidSolvent3×HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

0.44 ml of acetic acid was added to a solution of 510 mg of the product of Step B of Example 1, 7 ml of methanol and 2 ml of water another 0.44 ml of acetic acid was added. The mixture was cooled to 20° C. and 2.82 mg of sodium cyanide were added, after which the mixture was stirred for 90 minutes at 20° C., then cooled to ±10° C. Another 1.4 g of sodium cyanide and 2.2 ml of acetic acid were added and after stirring for 4 hours, the reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with water and dried, then concentrated to dryness to obtain 590 mg of α-hydroxy-1-(2-propynyl)-1H-pyrrole-3-acetonitrile.

Workup

  1. additionwas added
  2. temperaturecooled to ±10° C
  3. stirringafter stirring for 4 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water
  6. customdried
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8a90184c6150499bb55339b05165114a
Source dataset
uspto-grants-1989_01
Patent number
US04798901

Reaction notes

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