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Hydrochloric Acid → (Z)-5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylacetaldehyde

HRID 1420721
Notes
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Reaction equation

HRID 1420721 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][C:22](OC)=[O:23].[H-].C([Al+]CC(C)C)C(C)C.CO.Cl>C1(C)C=CC=CC=1.O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][CH:22]=[O:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 16046334Sulindac Sulfide Methyl EsterHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 86745520(Z)-5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylacetaldehyde

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 1140TolueneSolvent2×

Conditions

Temperature
-70 °C

Procedure

To a solution of the ester from Step 1 (3.39 g, 9.57 mmol) in toluene (75 mL) at -70° C., there was slowly added diisobutyl aluminum hydride (1M) in toluene (12 mL, 12 mmol) and the resulting mixture stirred at -70° C. for 45 minutes. Methanol (10 mL) was added slowly at -70° C., then the mixture was warmed to room temperature and water (100 mL) and 1N aqueous HCl (50 mL) were added. The mixture was shaken and the organic layer collected; the aqueous fraction was extracted with ether and the combined organic fractions washed 3 times with water, dried over MgSO4 and evaporated down to a thick oil. The crude title compound was used as such in the next step.

Workup

  1. customat -70° C.
  2. temperaturethe mixture was warmed to room temperature
  3. stirringThe mixture was shaken
  4. customthe organic layer collected
  5. extractionthe aqueous fraction was extracted with ether
  6. washthe combined organic fractions washed 3 times with water
  7. dry with materialdried over MgSO4
  8. customevaporated down to a thick oil

Sources & evidence

ORD record
ord-c7c4da16d7aa4f4c8e7bf7a64d7cadd6
Source dataset
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06071934

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes