Diethyl Ether → 6-[(6-Hydroxy-3,7,7-trimethyl-2-octenyl)-oxy]-2,3-dihydrobenzofuran

HRID 1414833Notes

Reaction equation

HRID 1414833 reaction equation
[O:1]=[CH:2][CH2:3][CH2:4][C:5]([CH3:18])=[CH:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]2[CH2:13][CH2:14][O:15][C:11]=2[CH:10]=1.C(OCC)C.[C:24]([Li])([CH3:27])([CH3:26])[CH3:25]>CCCCC>[OH:1][CH:2]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:3][CH2:4][C:5]([CH3:18])=[CH:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]2[CH2:13][CH2:14][O:15][C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 537384466-[(2,3-Dihydro-1-benzofuran-6-yl)oxy]-4-methylhex-4-enalHCID 178418306HCID 178418306, compound

Product 1

HCID 538917066-[(6-Hydroxy-3,7,7-trimethyl-2-octenyl)-oxy]-2,3-dihydrobenzofuran

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

1.94 g. of 6-[(6-oxo-3-methyl-2-hexenyl)-oxy]-2,3-dihydrobenzofuran are dissolved in 80 ml. of absolute diethyl ether and treated dropwise at 0° C. under nitrogen over a period of 20 minutes with 5 ml. of a 2-M solution of tertbutyl lithium in pentane. The mixture is then poured into ice-cold saturated aqueous ammonium chloride solution and extracted twice with diethyl ether. The extracts are dried over sodium sulfate and evaporated. There is obtained crude 6-[(6-hydroxy-3,7,7-trimethyl-2-octenyl)-oxy]-2,3-dihydrobenzofuran which is used in the process without further purification.

Workup

  1. additionThe mixture is then poured into ice-cold saturated aqueous ammonium chloride solution
  2. extractionextracted twice with diethyl ether
  3. dry with materialThe extracts are dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-d3d067be169f4c2ea558d5f137f5264f
Source dataset
uspto-grants-1977_01
Patent number
US04002647

Reaction notes

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