Water → Chloroform trifluoroacetic acid
Reaction equation
N(C1COC(CC(OC)OC)OC1)=[N+]=[N-].O.[C:17]([OH:23])([C:19]([F:22])([F:21])[F:20])=[O:18].[CH:24]([Cl:27])([Cl:26])[Cl:25]>>[C:17]([OH:23])([C:19]([F:22])([F:21])[F:20])=[O:18].[CH:24]([Cl:27])([Cl:26])[Cl:25]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
5-azido-2-(2,2-dimethoxyethyl)-1,3-dioxane 40 (33.65 g, 155 mmol) was dissolved in CHCl3 (1 L) with water (6.25 mL, 347 mmol) and cooled to 0° C. TFA (250 mL, 3.366 mol) was added to the reaction mixture to give 20% TFA/CHCl3 which was stirred at 0° C. for 40 min. The reaction was quenched with solid NaHCO3 (400 g, 4.76 mol) at 0° C. The reaction mixture was filtered and concentrated. The resulting aldehyde was used in the next step without further purification.
Sources & evidence
- ORD record
- ord-0f397752177848f1a85a4733035e5cba
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969405B2
Reaction notes
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