Hydrochloric Acid → Hexahydrofuro(2,3-b)furan-3-ol

HRID 78752Notes

Reaction equation

HRID 78752 reaction equation
[BH4-].[Li+].C(OC(=O)[C:7]([CH:9]1[CH2:13][CH2:12][O:11][CH:10]1[O:14][CH3:15])=[O:8])C.Cl.C(N(CC)CC)C>C1COCC1>[O:14]1[CH:10]2[O:11][CH2:12][CH2:13][CH:9]2[CH:7]([OH:8])[CH2:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 4148881Lithium borohydrideHCID 67609631HCID 67609631, compound

Product 1

HCID 9898832Hexahydrofuro(2,3-b)furan-3-olYield 46.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
67.5 °C

Procedure

2 M Lithium borohydride solutions (24.7 ml) was added to the flask under nitrogen atmosphere. Ethyl-2-(2-methoxytetrahydrofuran-3-yl)-2-oxoacetate (5 g) was dissolved in THF (25 ml) and slowly added at 65-70° C. Reaction mass was then maintained at 65-70° C. for 10 hrs. Reaction mass was cooled to −10° C. and slowly added concentrated hydrochloric acid (16 ml) and stirred for 2 hrs at −5 to 0° C. Triethyl amine (14.6 ml) was added to the reaction mass. Reaction mass was concentrated under vacuum. Ethyl acetate (20 ml) was added and again concentrated to residue. Ethyl acetate (50 ml) was added to it and filtered the un-dissolved salts. Filtrate was concentrated to get residue of Hexahydrofuro[2,3-b]furan-3-ol (yield 1.5 g).

Workup

  1. additionslowly added at 65-70° C
  2. customReaction mass
  3. customReaction mass
  4. temperaturewas cooled to −10° C.
  5. customReaction mass
  6. concentrationwas concentrated under vacuum
  7. additionEthyl acetate (20 ml) was added
  8. concentrationagain concentrated to residue
  9. additionEthyl acetate (50 ml) was added to it
  10. filtrationfiltered the un-dissolved salts
  11. concentrationFiltrate was concentrated

Sources & evidence

ORD record
ord-7de6b855cac942bb8cde562ed1da7b6a
Source dataset
uspto-grants-2014_09
Patent number
US08841467B2

Reaction notes

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