Iodine → 2,5-Bis-hydroxymethyl-2,3-dihydrobenzofuran

HRID 256402Notes

Reaction equation

HRID 256402 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][C:6]2[CH:8]=[C:9]([C:12](OCC)=[O:13])[CH:10]=[CH:11][C:5]=2[O:4]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].COCC1CC2C=C(C(OCC)=O)C=CC=2O1.II>O1CCCC1.C(OCC)(=O)C.CCCCCC>[OH:1][CH2:2][CH:3]1[CH2:7][C:6]2[CH:8]=[C:9]([CH2:12][OH:13])[CH:10]=[CH:11][C:5]=2[O:4]1

Participants

7

Reactant 4

HCID 807IodineHCID 13728720Ethyl 2-hydroxymethyl-2,3-dihydrobenzofuran-5-carboxylate2×HCID 20163636Ethyl 2-methoxymethyl-2,3-dihydrobenzofuran-5-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 201636522,5-Bis-hydroxymethyl-2,3-dihydrobenzofuranYield 83.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Reduction of 444 mg (2 mmole) ethyl 2-hydroxymethyl-2,3-dihydrobenzofuran-5-carboxylate, Preparation A, Part (iii), in 15 ml tetrahydrofuran with lithium aluminum hydride, 155 mg (4 mmole), by the method of Preparation A, Part iv), afforded 0.3 g of 2,5-bis-hydroxymethyl-2,3-dihydrobenzofuran as an oil, TLC 1:2 ethyl acetate/hexane, Rf 0.2, iodine positive. 1H-NMR(CDCl3)ppm(delta): 3.6 (CH2OH at 2-position), 4.6 (CH2OH at 5-position).

Sources & evidence

ORD record
ord-cd4ae05e074a4a5b937c96b22bc646aa
Source dataset
uspto-grants-1987_10
Patent number
US04703052

Reaction notes

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