Dimethylformamide → 343857-09-0

HRID 855293Notes

Reaction equation

HRID 855293 reaction equation
C1(C2C=CC([CH:8]=[O:9])=CC=2)CC1.Br[C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[C:18]([CH3:23])([CH3:22])[CH2:17][CH2:16]2.[Li]CCCC.CN(C=O)C>>[CH3:22][C:18]1([CH3:23])[C:19]2[C:15](=[CH:14][C:13]([CH:8]=[O:9])=[CH:21][CH:20]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 115064744-CyclopropylbenzaldehydeHCID 124417845-Bromo-1,1-dimethyl-2,3-dihydro-1H-indeneHCID 178418339Butyllithium

Product 1

HCID 12859396343857-09-0Yield 93%

Procedure

The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S53) using 5-bromo-1,1-dimethylindan [synthesized in analogy to a procedure described in Org. Prep. Proc. Int. 10:123-131 (1978)] (270 mg, 1.20 mmol), nBuLi (833 μl, 1.6M solution in hexane, 1.33 mmol) and DMF (173 μl, 2.22 mmol). The isolated residue was purified by flash column chromatography (1:9 ether:pentane) to give 1,1-dimethylindan-5-carbaldehyde (195 mg, 93%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 9.96 (s, 1H), 7.71-7.69 (m, 2H), 7.28 (m, 1H), 2.95 (apt t, J=7.0 Hz, 2H), 1.98 (apt t, J=7.0 Hz, 2H), 1.95 (s, 6H).

Workup

  1. customsynthesized in analogy to a procedure
  2. customThe isolated residue was purified by flash column chromatography (1:9 ether:pentane)

Sources & evidence

ORD record
ord-93c2ed093d2344fa9346fd9500f0128a
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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