Water → HCID 66936522, compound

HRID 1929244Notes

Reaction equation

HRID 1929244 reaction equation
[CH2:1]([N:8]([CH3:16])[C:9]([C@H:11]1[CH2:15][CH2:14][CH2:13][O:12]1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[O:12]1[CH2:13][CH2:14][CH2:15][C@@H:11]1[CH2:9][N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 975398HCID 975398, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 66936522HCID 66936522, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 24.60 g of (R)-tetrahydrofuran-2-carboxylic acid-N-benzyl-N-methylamide in 90 ml tetrahydrofuran is added dropwise to 17.00 g of lithium aluminium hydride in 150 ml of tetrahydrofuran. The reaction mixture is refluxed for two hours. For working up it is cooled to 0° C. in an ice bath, mixed with 20 ml of water and 10 ml of 15 N sodium hydroxide solution and stirred for another 20 minutes. Then it is filtered through a layer of magnesium sulfate and washed with a total of about 500 ml of tetrahydrofuran. The filtrate is evaporated down in vacuo, leaving a yellowish oil which is further reacted without any more purification. Yield: 21.10 g (92% of theory); mass spectrum (ESI+): m/z=206 [M+H]+.

Workup

  1. temperatureThe reaction mixture is refluxed for two hours
  2. filtrationThen it is filtered through a layer of magnesium sulfate
  3. washwashed with a total of about 500 ml of tetrahydrofuran
  4. customThe filtrate is evaporated down in vacuo
  5. customleaving a yellowish oil which
  6. customis further reacted without any more purification

Sources & evidence

ORD record
ord-f10239ef3a1d49cca729f818bdff3931
Source dataset
uspto-grants-2012_05
Patent number
USRE043431E1

Reaction notes

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