Acetyl chloride → HCID 12889243, compound

HRID 716144Notes

Reaction equation

HRID 716144 reaction equation
[C:1](Cl)(=O)C.[OH:5][C@@H:6]1[C@H:10]([OH:11])[CH:9]([OH:12])[O:8][C@@H:7]1[CH2:13][OH:14].C[O-].[Na+].CO>CO.C1(C)C=CC=CC=1>[OH:5][C@@H:6]1[C@H:10]([OH:11])[CH:9]([O:12][CH3:1])[O:8][C@@H:7]1[CH2:13][OH:14]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 11435035D-LYXOFURANOSEHCID 23694274Sodium methanolate methanol

Product 1

HCID 12889243HCID 12889243, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1140TolueneSolvent

Procedure

720 mL of acetyl chloride was added dropwise to 1200 mL of a methanol solution of 12.0 kg of (2R,3R,4S)-3,4,5-trihydroxy-2-hydroxymethyloxolane at a temperature of 15° C. or lower over 30 minutes, and the obtained mixture was then stirred at a temperature of 20° C. to 30° C. for 1 hour. Thereafter, 2100 mL of a 28% sodium methoxide/methanol solution and 1000 mL of toluene were added to the reaction mixture, and methanol was then distilled away under reduced pressure, to obtain 4500 mL of a toluene solution of (2R,3R,4S)-3,4-dihydroxy-2-hydroxymethyl-5-methoxyoxolane.

Workup

  1. distillationwas then distilled away under reduced pressure

Sources & evidence

ORD record
ord-f392613dd5914769bf129c4cbc877c77
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

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