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

HRID 379620Notes

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]

Participants

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

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

Sources & evidence

ORD record: ord-a488b634b7a942aaa0af4e680cac5850
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300346B1

Reaction notes

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