Water → HCID 22244497, compound

HRID 1274485Notes

Reaction equation

HRID 1274485 reaction equation
[CH3:1][C:2]1([CH3:13])[O:7][CH:6]([C:8]([CH3:12])([CH3:11])[CH:9]=[O:10])[CH2:5][CH2:4][O:3]1.[CH3:14][CH2:15][Mg+].[Br-].[NH4+].[Cl-].O>C(OCC)C>[CH3:1][C:2]1([CH3:13])[O:7][CH:6]([C:8]([CH3:12])([CH:9]([OH:10])[CH2:14][CH3:15])[CH3:11])[CH2:5][CH2:4][O:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 21914222HCID 21914222, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 22244497HCID 22244497, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 268 mg (1.44 mmol) of aldehyde 45 in 4 ml of diethyl ether is mixed at 0° C. with 528 μl (1.58 mmol, 1.1 equivalents) of a 3 M solution of EtMgBr in ether. It is allowed to stir for 2 hours at 0° C., heated to room temperature and allowed to stir for another hour. For working-up, it is mixed with saturated aqueous NH4Cl solution, and then water is added steadily until the precipitate goes into solution. The aqueous phase is extracted with ether, the combined organic phases are dried on MgSO4 and concentrated by evaporation. The residue is purified by column chromatography with pentane:ether=1:1. 251 mg (1.16 mmol) of alcohol 46, corresponding to a yield of 80%, is obtained.

Workup

  1. temperatureheated to room temperature
  2. stirringto stir for another hour
  3. extractionThe aqueous phase is extracted with ether
  4. customthe combined organic phases are dried on MgSO4
  5. concentrationconcentrated by evaporation
  6. customThe residue is purified by column chromatography with pentane

Sources & evidence

ORD record
ord-5253549dbdbc466a80fc6ee6897bbe58
Source dataset
uspto-grants-2000_12
Patent number
US06156905

Reaction notes

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