Lithium Hydroxide → (3R,3aS,6aR)-hexahydrofuro(2,3-b)furan-3-ol

HRID 896834Notes

Reaction equation

HRID 896834 reaction equation
[OH:1][C@H:2]1[C@H:9]2[C@H:5]([O:6][CH2:7][CH2:8]2)[O:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+](C1C=CC(C(O)=O)=CC=1)([O-])=O.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Li+].[OH-]>C1C=CC=CC=1.O.CCN(CC)CC>[OH:1][C@@H:2]1[C@H:9]2[C@H:5]([O:6][CH2:7][CH2:8]2)[O:4][CH2:3]1

Participants

9

Reactant 5

HCID 3939Lithium HydroxideHCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11147731(3S,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol

Product 1

HCID 9942150(3R,3aS,6aR)-hexahydrofuro(2,3-b)furan-3-olYield 82%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of alcohol (5) (400 mg, 3.07 mmol), triphenylphosphine (1.6 g, 61.4 mmol), and p-nitrobenzoic acid (770 mg, 4.61 mmol) in dry benzene (30 mL) at 23° C. was added diisoproylazodicarboxylate (DIAD, 1.2 mL, 6.14 mmol) dropwise. After 1.5 hours, the mixture was concentrated in vacuo, and the crude ester was dissolved in a (4:3:1) mixture of MeOH:Et3N:H2O (24 mL), then treated with LiOH (450 mg, 10.7 mmol). The solution was stirred at room temperature for 2 h. The mixture then was concentrated under reduced pressure and the residue was chromatographed over silica gel to provide the bis-THF (I) (326 mg, 82%); [α]25D −12.4 (c 1.16, MeOH).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionthe crude ester was dissolved in a (4:3:1) mixture of MeOH
  3. concentrationThe mixture then was concentrated under reduced pressure
  4. customthe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-4b86acf25fb043b6a7c497c9ed73a3d4
Source dataset
uspto-grants-2005_07
Patent number
US06919465B2

Reaction notes

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