Fluorene-2-carboxaldehyde → HCID 57801038, compound

HRID 1817682Notes

Reaction equation

HRID 1817682 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[CH:14]=[O:15].Br[CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21].[Mg]>C(OCC)C.COCCOCCOC.C(Cl)Cl>[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[CH:14]([OH:15])[CH2:21][CH2:20][CH2:19][CH:18]=[CH2:17]

Participants

7

Reactant 3

HCID 34804Fluorene-2-carboxaldehydeHCID 707041-Pentene, 5-bromo-HCID 5462224Magnesium

Product 1

HCID 57801038HCID 57801038, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8150DiglymeSolvent

Procedure

2-Fluorenecarboxaldehyde (3 g) was dissolved in a mixture of anhydrous diethyl ether (30 ml) and anhydrous diglyme (5 ml) and was reacted with a grignard prepared from 5-bromopentene and magnesium, as described for example 23. The mixture was stirred for 30 min and a precipitate filtered off and washed with diethyl ether to give a white powder. The powder was dissolved in DCM and washed with saturated NH4Cl and water. Evaporation gave an oil which rapidly solidified. Column chromatography gave the title compound as a white solid. δC (CDCl3, 62.9 MHz): 25.2, 33.7, 36.9, 38.7, 74.8, 114.8, 119.8, 119.9, 122.6, 124.7, 125.1, 126.7, 126.8, 138.7, 141.2, 141.5, 143.4, 143.6 and 143.6.

Workup

  1. customwas reacted with a grignard
  2. filtrationa precipitate filtered off
  3. washwashed with diethyl ether
  4. customto give a white powder
  5. washwashed with saturated NH4Cl and water
  6. customEvaporation
  7. customgave an oil which

Sources & evidence

ORD record
ord-7f93b41dad9940db95006d2f5fdcd695
Source dataset
uspto-grants-2009_10
Patent number
US07598289B2

Reaction notes

Loading…