Ammonium Chloride → HCID 21964441, compound

HRID 406807Notes

Reaction equation

HRID 406807 reaction equation
[S:1]1[C:5]([CH2:6][CH:7]=[O:8])=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[C:13]([Mg]Br)#[CH:14].[NH4+].[Cl-]>C1COCC1>[S:1]1[C:5]([CH2:6][CH:7]([OH:8])[C:13]#[CH:14])=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 19912860HCID 19912860, compoundHCID 178418486HCID 178418486, compound

Product 1

HCID 21964441HCID 21964441, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of crude 9-3 (8.77 g) in THF (100 mL) was added to a solution of ethynylmagnesium bromide (450 mL, 225 mmol, 0.5 M/THF) at 0° C. by cannula. The mixture was stirred for 1 h at 0° C. and for 1 h at room temperature. The reaction was then queched by addition of 200 mL saturated NH4Cl solution. The layers were separated and the aqueous layer was extracted with ethyl acetate (3×200 mL). The combined organic solution was washed with brine and then was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (10% 20% ethyl acetate/hexanes) gave 8-4 (7.67 g, 37.9 mmol, 84% from 9-2).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×200 mL)
  3. washThe combined organic solution was washed with brine
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by flash chromatography on silica gel (10% 20% ethyl acetate/hexanes)
  8. customgave 8-4 (7.67 g, 37.9 mmol, 84% from 9-2)

Sources & evidence

ORD record
ord-c9adfe92e28e45c5b51462bc699509cb
Source dataset
uspto-grants-2014_06
Patent number
US08754122B2

Reaction notes

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