Hydrochloric Acid → HCID 57420145, compound

HRID 1172835Notes

Reaction equation

HRID 1172835 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:16]=[CH:15][C:10]([C:11](OC)=[O:12])=[C:9]([CH2:17][CH2:18][CH3:19])[N:8]=2)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[N:8]=[C:9]([CH2:17][CH2:18][CH3:19])[C:10]([CH2:11][OH:12])=[CH:15][CH:16]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 57420144HCID 57420144, compound

Product 1

HCID 57420145HCID 57420145, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the product from Step 3 (48 g, 157 mmol) in toluene (500 mL) cooled at −75° C. was added a solution of diisobutylaluminum hydride (1.0 M in toluene, 314 mL, 314 mmol) over a 45 min period. After additional 30 min at −75° C., the reaction mixture was poured into a ice-cold solution of 1 N hydrochloric acid (1.5 L) and the mixture was stirred at room temperature for 30 min. The product was extracted with ethyl acetate (2×500 mL) and organic extracts were washed with a saturated solution of sodium bicarbonate and brine. After removal of the solvent, the crude product was purified by chromatography on silica gel eluting with 7:1 hexane:ethyl acetate to give the title product as an oil.

Workup

  1. extractionThe product was extracted with ethyl acetate (2×500 mL) and organic extracts
  2. washwere washed with a saturated solution of sodium bicarbonate and brine
  3. customAfter removal of the solvent
  4. customthe crude product was purified by chromatography on silica gel eluting with 7:1 hexane

Sources & evidence

ORD record
ord-7a26f91eae78420db31ac7e933cc27f5
Source dataset
uspto-grants-2010_11
Patent number
US07834036B2

Reaction notes

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