Hydrochloric Acid → HCID 14461328, compound

HRID 1073097Notes

Reaction equation

HRID 1073097 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14]([C:16]1[C:20]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:22]=2)=[C:19]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:18][C:17]=1[CH:41]([CH3:43])[CH3:42])=O)C.CC(C[AlH]CC(C)C)C.Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[F:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]2[C:16]([CH2:14][OH:13])=[C:17]([CH:41]([CH3:43])[CH3:42])[O:18][C:19]=2[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[CH:22][C:23]=1[O:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 14461327HCID 14461327, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 14461328HCID 14461328, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-70 °C

Procedure

70 ml (84 mmol) of a 1.2M diisobutylaluminum hydride solution in toluene are slowly added dropwise at -78° C. under an argon atmosphere to a solution of 31 g (70 mmol) of the compound from Example 23 in 350 ml of anhydrous toluene in such a way that the temperature does not exceed -65° C. After stirring for 1 hour at -70° C., a further 58 ml (70 mmol) of DIBAH solution are added and the mixture is stirred for 1 more hour. 240 ml of 1N hydrochloric acid are then added dropwise at about -30° C. and finally 400 ml of water and 200 ml of ethyl acetate are added, as a result of which the mixture warms to room temperature. The aqueous phase is extracted 3 times with 250 ml of ethyl acetate, and the washed organic phases are washed with 400 ml of water and 400 ml of saturated sodium chloride solution and dried over sodium sulphate. The solvent is removed and the residue is dried under high vacuum.

Workup

  1. customdoes not exceed -65° C
  2. stirringthe mixture is stirred for 1 more hour
  3. customas a result of which the mixture
  4. customwarms to room temperature
  5. extractionThe aqueous phase is extracted 3 times with 250 ml of ethyl acetate
  6. washthe washed organic phases are washed with 400 ml of water and 400 ml of saturated sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. customThe solvent is removed
  9. customthe residue is dried under high vacuum

Sources & evidence

ORD record
ord-da92a015df6c437a81add54931db3ee2
Source dataset
uspto-grants-1990_11
Patent number
US04968681

Reaction notes

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