Lithium Chloride → delta-Gluconolactone

HRID 718204Notes

Reaction equation

HRID 718204 reaction equation
C[Si](C)(C)[O:3][C@@H:4]1[C@@H:9]([O:10][Si](C)(C)C)[C@H:8]([O:15][Si](C)(C)C)[C@@H:7]([CH2:20][O:21][Si](C)(C)C)[O:6][C:5]1=[O:26].C([Mg]Cl)(C)C.[Li+].[Cl-]>CCCCCCC>[CH2:20]([OH:21])[C@H:7]1[O:6][C:5](=[O:26])[C@H:4]([OH:3])[C@@H:9]([OH:10])[C@@H:8]1[OH:15]

Participants

5

Reactant 3

HCID 433294Lithium ChlorideHCID 10994280(3R,4S,5R,6R)-3,4,5-Tris-trimethylsilanyloxy-6-trimethylsilanyloxymethyl-tetrahydro-pyran-2-onHCID 178418918HCID 178418918, compound

Product 1

HCID 7027delta-Gluconolactone

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
-15 °C

Procedure

A 500 L glass-lined reactor was charged with (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)tetrahydro-2H-pyran-2-one (11.4 kg) and n-heptane (12.2 kg) and the mixture was cooled to −15° C. under nitrogen sparging for 1 h. iPrMgCl.LiCl (0.5 kg, 1.3 M in THF) was added dropwise and the mixture was stirred for 30 min at −15° C.

Sources & evidence

ORD record
ord-16b65c67d59d4e7fa9ecf7a2b275315e
Source dataset
uspto-grants-2015_11
Patent number
US09193751B2

Reaction notes

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