Ammonium Chloride → 5-(3-Chloro-benzo[b]thiophen-2-yl)-pent-1-yn-3-ol

HRID 406800Notes

Reaction equation

HRID 406800 reaction equation
[Cl:1][C:2]1[C:3]2[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[CH2:7][CH2:8][CH:9]=[O:10].[C:15]([Mg]Br)#[CH:16].[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[C:3]2[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[CH2:7][CH2:8][CH:9]([OH:10])[C:15]#[CH:16]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 219644333-(3-Chloro-benzo[b]thiophen-2-yl)-propionaldehydeHCID 178418486HCID 178418486, compound

Product 1

HCID 219644275-(3-Chloro-benzo[b]thiophen-2-yl)-pent-1-yn-3-olYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of aldehyde 17 (2.11 g, 9.4 mmol) in 15 mL THF was added to a solution of ethynylmagnesium bromide (28.2 mL, 14.1 mmol, 0.5 M THF) at 0° C. After 1.5 h, saturated NH4Cl solution (75 mL) was added and the mixture was extracted with ethyl acetate (3×50 mL). The combined ethyl acetate solution was washed with brine (50 mL) and then was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (5-20% ethyl acetate/hexane) gave 2.20 g (8.78 mmol, 93%) of the alcohol (18).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  2. washThe combined ethyl acetate solution was washed with brine (50 mL)
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography (5-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-21993a6e3cad490b987f6ca92e93f02b
Source dataset
uspto-grants-2014_06
Patent number
US08754122B2

Reaction notes

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