delta-Gluconolactone → HCID 86714018, compound

HRID 576302Notes

Reaction equation

HRID 576302 reaction equation
[Br:1][C:2]1[C:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:9][C:8](Br)=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2.[Li][CH2:22][CH2:23][CH2:24][CH3:25].[CH2:26]([OH:37])[C@H:27]1[O:33][C:31](=[O:32])[C@H:30]([OH:34])[C@@H:29]([OH:35])[C@@H:28]1[OH:36]>C1COCC1>[CH2:22]([O:34][C@@H:30]1[C@@H:29]([O:35][CH2:22][C:23]2[CH:4]=[CH:5][CH:6]=[CH:25][CH:24]=2)[C@H:28]([O:36][CH2:22][C:23]2[CH:13]=[CH:12][CH:17]=[CH:25][CH:24]=2)[C@@H:27]([CH2:26][O:37][CH2:11][C:10]2[CH:9]=[CH:8][CH:7]=[CH:3][CH:2]=2)[O:33][C:31]1([C:8]1[CH:9]=[C:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:2]([Br:1])=[C:3]2[C:7]=1[CH2:6][CH2:5][CH2:4]2)[OH:32])[C:23]1[CH:16]=[CH:15][CH:14]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7027delta-GluconolactoneHCID 86714015HCID 86714015, compoundHCID 178418339Butyllithium

Product 1

HCID 86714018HCID 86714018, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of bromide 6 (3.21 g, 8.10 mmol) in anhydrous THF (28.3 mL) was added dropwise n-BuLi (2.5M in hexane, 3.40 mL, 8.51 mmol) at −78° C. under nitrogen atmosphere, and the mixture was stirred for 0.5-1 h at the same temperature. Then a solution of perbenzylated gluconolactone 13 (4.37 g, 8.10 mmol) in THF (9.6 mL) was added dropwise, and the mixture was stirred for 3 h at the same temperature. The reaction mixture was quenched with saturated NH4Cl solution (30 mL) and extracted with EtOAc (100 mL). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to provide the crude intermediate 16, which was used without further purification (6.96 g, 8.13 mmol, 100%).

Workup

  1. stirringthe mixture was stirred for 3 h at the same temperature
  2. customThe reaction mixture was quenched with saturated NH4Cl solution (30 mL)
  3. extractionextracted with EtOAc (100 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd482ed0ffbf4fa4991941c0b9c1bb2b
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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