Ammonium Chloride → HCID 85830276, compound

HRID 1988224Notes

Reaction equation

HRID 1988224 reaction equation
CON(C)[C:4](=[O:10])[CH2:5][CH2:6][CH:7]([OH:9])[CH3:8].[CH2:12]=[CH:13][CH2:14][CH2:15][CH2:16]C.[Br-].[Mg+2].[Br-].[Cl-].[NH4+]>O1CCCC1>[OH:9][CH:7]([CH2:6][CH2:5][C:4](=[O:10])[CH2:16][CH2:15][CH2:14][CH:13]=[CH2:12])[CH3:8]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 791932134-Hydroxy-pentanoic acid methoxy-methyl-amideHCID 86601651HCID 86601651, compound

Product 1

HCID 85830276HCID 85830276, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 4-hydroxy-pentanoic acid methoxy-methyl-amide (0.12 g, 0.74 mmol) in tetrahydrofuran (1 mL) was cooled to −78° C., after which a solution of hex-1-ene-magnesium bromide (7.0 ml, 1.56 mmol) was added dropwise. After stirring at −78° C. for 2 hours, saturated ammonium chloride (2 mL) was added, and the reaction mixture allowed to warm to room temperature. Extraction and chromatography afforded 2-hydroxy-dec-9-en-5-one as a clear oil (33 mg).

Workup

  1. temperatureto warm to room temperature
  2. extractionExtraction and chromatography

Sources & evidence

ORD record
ord-ab2eade314464fe3a8c67bb3c359db1d
Source dataset
uspto-grants-2009_06
Patent number
US07553979B2

Reaction notes

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