Dimethylformamide → 2-Dipropylamino-indan-5-carbaldehyde

HRID 725923Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([N:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])[CH2:8]2)=[CH:4][CH:3]=1.[Li]C(C)(C)C.CCCCC.CN([CH:31]=[O:32])C>C(OCC)C>[CH2:12]([N:11]([CH2:15][CH2:16][CH3:17])[CH:7]1[CH2:8][C:9]2[C:5](=[CH:4][CH:3]=[C:2]([CH:31]=[O:32])[CH:10]=2)[CH2:6]1)[CH2:13][CH3:14]

Participants

Conditions

Temperature: -78 °C

Procedure

Distilled (6-bromo-indan-2-yl)-dipropyl-amine (Example 11, 270 mg, 0.91 mmol) was dissolved in dry diethyl ether (20 mL). The solution was kept under argon and cooled to -78° C. A solution of t-BuLi in pentane 1.7M (0.7 mL, 1.20 mmol) was added and the mixture was stired at -78° C. for 1 h. Freshly distilled DMF (0.12 mL, 1.55 mmol) was added at -78° C. and the mixture was stirred at this temperature for 30 min. The reaction mixture was allowed to reach room temperature and stirred for additional 1 h. The organic layer was washed with aq. Na2CO3 (5%), the layers separated, dried (Na2CO3) and evaporated to dryness. MS m/e 245 (11, M+), 216 (100), 145 (17), 117 (22), 72 (21).

Workup

customto reach room temperature
stirringstirred for additional 1 h
washThe organic layer was washed with aq. Na2CO3 (5%)
customthe layers separated
dry with materialdried (Na2CO3)
customevaporated to dryness

Sources & evidence

ORD record: ord-f7d42cfae395438e91ab371167cb792e
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05708018

Reaction notes

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