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

HRID 1449360Notes

Reaction equation

HRID 1449360 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): δ3.59 (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-c8e25559da554a5eb39ad2eb466c0fac
Source dataset
uspto-grants-1980_02
Patent number
US04190596

Reaction notes

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