Water → HCID 77230206, compound

HRID 602241Notes

Reaction equation

HRID 602241 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([C:9]([O:20][Si](C)(C)C)([C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10][CH:11]([CH3:13])[CH3:12])#[N:8].O.[OH-].[Na+]>C(OCC)C>[CH2:10]([C:9]([OH:20])([C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:7][NH2:8])[CH:11]([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 77230207HCID 77230207, compound

Product 1

HCID 77230206HCID 77230206, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Under a nitrogen atmosphere, 6.3 g of LiAlH4 (0.167 moles) are suspended in 250 mL of anhydrous diethyl ether and the temperature is reduced to 0° C. 43 g of (1b) (0.162 moles) in 75 mL of anhydrous diethyl ether are added dropwise and the mixture is stirred for 20 h. LiAlH4 is hydrolysed with water and 30% NaOH and the phases are separated. The aqueous phase is extracted repeatedly with diethyl ether, the organic phase is extracted with 1N HCl, the aqueous phase is alkalised with 30% NaOH, extracted with diethyl ether, the combined organic phases are washed to neutrality, dried with Na2SO4 and evaporated. 20.8 g of product are obtained, which are used in the subsequent step without further purification. Formula: C12H23NO (m.w. 197.32). Yield 65%.

Workup

  1. customis reduced to 0° C
  2. customthe phases are separated
  3. extractionThe aqueous phase is extracted repeatedly with diethyl ether
  4. extractionthe organic phase is extracted with 1N HCl
  5. extractionextracted with diethyl ether
  6. washthe combined organic phases are washed to neutrality
  7. dry with materialdried with Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-5389f824e6624019ac1a8b3a229de401
Source dataset
uspto-grants-2011_03
Patent number
US07906501B2

Reaction notes

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