Toluene → HCID 22481030, compound

HRID 412685Notes

Reaction equation

HRID 412685 reaction equation
[CH:1]1([C:6]2[C:15]([CH:16](F)[C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[C:14]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[CH:29]=3)[C:13]3[CH:12]([OH:36])[CH2:11][C:10]([CH3:38])([CH3:37])[CH2:9][C:8]=3[N:7]=2)CC[CH2:3][CH2:2]1.C1(C)C=CC=CC=1.C([Al]CC(C)C)C(C)C.[Cl-].[Na+]>CO>[CH:1]1([C:6]2[C:15]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[C:14]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[CH:29]=3)[C:13]3[CH:12]([OH:36])[CH2:11][C:10]([CH3:37])([CH3:38])[CH2:9][C:8]=3[N:7]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 5234Sodium ChlorideHCID 16682954DibahHCID 22481040HCID 22481040, compound

Product 1

HCID 22481030HCID 22481030, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-70 °C

Procedure

280 mg (0.52 mmol) of the compound from Example 4 are dissolved in 40 ml of abs. toluene and, at from −10° C. to −15° C., admixed dropwise with 3.5 ml of 25% strength diisobutylaluminium hyride solution. The mixture is stirred for 1 hour, cooled to −70° C. and admixed dropwise with 0.2 ml of methanol. At 20° C., the mixture is admixed with sodium chloride solution, the phases are separated and the organic phase is dried. The evaporation residue is purified over a silica gel column Crystallization from heptane gives 195 mg of colourless crystals of m.p. 126-127° C.

Workup

  1. customat from −10° C. to −15° C.
  2. customAt 20° C.
  3. customthe phases are separated
  4. customthe organic phase is dried
  5. customThe evaporation residue is purified over a silica gel column Crystallization from heptane

Sources & evidence

ORD record
ord-99675d1ee4d44401a93e890f709f64fa
Source dataset
uspto-grants-2003_05
Patent number
US06562976B2

Reaction notes

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