Water → HCID 24814178, compound

HRID 1183787Notes

Reaction equation

HRID 1183787 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([N:13]([C:24]2[CH:29]=[CH:28][C:27]([C:30](OC)=[O:31])=[CH:26][CH:25]=2)[C:14]2[CH:19]=[CH:18][C:17]([C:20](OC)=[O:21])=[CH:16][CH:15]=2)[CH:10]=[CH:9][C:4]=1[C:5](OC)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1.ClCCl>[OH:21][CH2:20][C:17]1[CH:16]=[CH:15][C:14]([N:13]([C:24]2[CH:25]=[CH:26][C:27]([CH2:30][OH:31])=[CH:28][CH:29]=2)[C:11]2[CH:10]=[CH:9][C:4]([CH2:5][OH:6])=[C:3]([O:2][CH3:1])[CH:12]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 24814177HCID 24814177, compound

Product 1

HCID 24814178HCID 24814178, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of compound 7 (1.35 g, 3 mmol) in 20 mL of THF is added dropwise to a suspension of lithium aluminium hydride (LiAlH4, 1.7 g, 45 mmol, 15 eq.) in dry tetrahydrofuran (THF) (30 mL) at −78° C. The temperature of the medium is allowed to return to room temperature and then the reaction is heated under reflux with stirring. After 1 hour, the solution is cooled to −78° C. and diluted with dichloromethane, and then water (10 mL) is slowly poured in. The solid obtained is filtered and washed with dichloromethane. The mother liquors are washed with water and with brine and then dried and concentrated to give 1.05 g (2.88 mmol) of a pasty compound (yield: 97%).

Workup

  1. customto return to room temperature
  2. temperaturethe reaction is heated
  3. temperatureunder reflux
  4. customThe solid obtained
  5. filtrationis filtered
  6. washwashed with dichloromethane
  7. washThe mother liquors are washed with water and with brine
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1a5a14bbd1f84301815b922e4b4f665f
Source dataset
uspto-grants-2014_03
Patent number
US08664400B2

Reaction notes

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