Sodium Sulfite → 2-(2,3-dihydro-1H-inden-2-yl)acetaldehyde

HRID 2293102Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH:12]1[CH2:20][C:21](OCC)=[O:22].S([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH:12]1[CH2:20][CH:21]=[O:22]

Participants

Conditions

Temperature: -78 °C

Procedure

Under cooling at -78° C., 1.5M diisobutyl aluminum hydride (DIBAH) dissolved in 65 ml of toluene was added to 19.34 g of ethyl 2-indanacetate dissolved in 200 ml of toluene. The mixture was stirred at the same temperature for 1.5 hours. A 15% sodium sulfite aqueous solution was added to the mixture. After the organic layer was collected by separation, washed and dried, the solvent was removed. The residue was purified by silica gel column chromatography (hexane-ethyl acetate (10:1)) to obtain 13.58 g of 2-indanacetaldehyde.

Workup

customAfter the organic layer was collected by separation
washwashed
customdried
customthe solvent was removed
customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate (10:1))

Sources & evidence

ORD record: ord-dbde515d60f649268e8412683ec0cef0
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686452

Reaction notes

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