Toluene → HCID 523407, compound

HRID 1047403Notes

Reaction equation

HRID 1047403 reaction equation
[C:1]1(=[O:12])[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].CN1CCOCC1.[CH3:20][Si:21](Cl)([CH3:23])[CH3:22].C1(C)C=CC=CC=1>O1CCCC1.O>[CH3:20][Si:21]([CH3:23])([CH3:22])[O:3][CH:2]1[CH:4]([O:5][Si:21]([CH3:23])([CH3:22])[CH3:20])[CH:6]([O:7][Si:21]([CH3:23])([CH3:22])[CH3:20])[CH:8]([CH2:9][O:10][Si:21]([CH3:23])([CH3:22])[CH3:20])[O:11][C:1]1=[O:12]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6397ChlorotrimethylsilaneHCID 7027delta-GluconolactoneHCID 79724-Methylmorpholine

Product 1

HCID 523407HCID 523407, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of D-(+)-glucono-1,5-lactone (7.88 kg) and N-methylmorpholine (35.8 kg) in tetrahydrofuran (70 kg) was added trimethylsilyl chloride (29.1 kg) at 40° C. or below, and then the mixture was stirred at a temperature from 30° C. to 40° C. for 2 hours. After the mixture was cooled to 0° C., toluene (34 kg) and water (39 kg) were added thereto. The organic layer was separated and washed with an aqueous solution of 5% sodium dihydrogen phosphate (39.56 kg×2) and water (39 kg×1). The solvent was evaporated under reduced pressure to give the titled compound as an oil. The product was used in the next step without further purification.

Workup

  1. customThe organic layer was separated
  2. washwashed with an aqueous solution of 5% sodium dihydrogen phosphate (39.56 kg×2) and water (39 kg×1)
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-dcc9216a3903481caa9f7744399de9bd
Source dataset
uspto-grants-2013_10
Patent number
US08569520B2

Reaction notes

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