Tetrahydrofuran → 1-(3,4-Dihydro-1h-isoquinolin-2-yl)-propynone

HRID 361608Notes

Reaction equation

HRID 361608 reaction equation
C([Mg]Br)#C.CON(C)[C:8]([N:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1)=O.[Cl-].[NH4+].[O:23]1CC[CH2:25][CH2:24]1>>[CH2:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][N:10]([C:8]#[C:25][CH:24]=[O:23])[CH2:19]1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 121859113,4-Dihydro-N-methoxy-N-methyl-2(1H)-isoquinolinecarboxamideHCID 178418486HCID 178418486, compound

Product 1

HCID 540951631-(3,4-Dihydro-1h-isoquinolin-2-yl)-propynoneYield 57%

Conditions

Temperature
0 °C

Procedure

9.08 ml of a 0.5 molar solution of ethynylmagnesium bromide in tetrahydrofuran were added dropwise within 20 min. to a solution of 1 g of 3,4-dihydro-1H-isoquinoline-2-carboxylic acid methoxy-methyl-amide in 5 ml of tetrahydrofuran under argon at 0° C. The reaction mixture was stirred at 0° C. for 1 h. and at room temperature for 1 h. The orange solution was poured into 50 ml of a saturated ammonium chloride solution and extracted twice with 50 ml of ethyl acetate each time. The combined organic phases were washed twice with 50 ml of water each time, once with 50 ml of a saturated sodium chloride solution, dried over magnesium sulfate and concentrated. 0.48 g (57%) of 1-(3,4-dihydro-1H-isoquinolin-2-yl)-propynone was obtained as a yellowish oil. MS (EI): 185M30 .

Workup

  1. extractionextracted twice with 50 ml of ethyl acetate each time
  2. washThe combined organic phases were washed twice with 50 ml of water each time
  3. dry with materialonce with 50 ml of a saturated sodium chloride solution, dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b9aa6c5390c74c08a6659c36ae2f36cb
Source dataset
uspto-grants-1999_02
Patent number
US05866583

Reaction notes

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