Furan → 5-Chloro-1-(2-furyl)-1-pentanol

HRID 1701119Notes

Reaction equation

HRID 1701119 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[Li].C([Li])CCC.O1C=CC=C1.[Cl:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23].[Cl-].[NH4+]>CCOCC.CCCCCC>[Cl:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)[OH:23]

Participants

8

Reactant 5

HCID 8029FuranHCID 25517Ammonium ChlorideHCID 789155-Chloro-1-pentanolHCID 178418296HCID 178418296, compoundHCID 178418339Butyllithium

Product 1

HCID 202925795-Chloro-1-(2-furyl)-1-pentanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 2-furyllithium [prepared from 0.53 moles of n-butyllithium and 39.5 g of furan by the procedure of J. Org. Chem., 27, 1216 (1962)] in 350 ml of ether and with 200 ml of hexane at -78° C. is added a solution of 57.9 g of 5-chloropentanol [Chem. Abstr., 59, 7579F (1963)] in 80 ml of ether during 25 minutes. The mixture is warmed to 0° C. during 20 minutes, stirred at 0° C. for 15 minutes, and treated with 140 ml of saturated ammonium chloride. The ether phase is washed with water and brine, dried over magnesium sulfate and potassium carbonate mixture, and concentrated to give a liquid, pmr spectrum (CDCl3): δ 3.59 (triplet, CH2Cl) and 4.70 (triplet, CH2CHOH).

Workup

  1. washThe ether phase is washed with water and brine
  2. dry with materialdried over magnesium sulfate and potassium carbonate mixture
  3. concentrationconcentrated
  4. customto give a liquid, pmr spectrum (CDCl3)

Sources & evidence

ORD record
ord-a9a25c29f5e4442d875c704fd7b166c7
Source dataset
uspto-grants-1980_03
Patent number
US04191699

Reaction notes

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