Tetrahydrofuran → HCID 21946203, compound
Reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3]C1.[CH3:6][C:7]([OH:12])([CH:9]([CH3:11])[CH3:10])[CH3:8].[CH2:13](N(CC)CC)C>>[C:5]([O:12][C:7]([CH3:8])([CH:9]([CH3:11])[CH3:10])[CH3:6])(=[O:1])[C:4]([CH3:13])=[CH2:3]Participants
Procedure
Into a 500 mL flask containing a stir bar, and fitted with a condenser, was placed 180 g of anhydrous tetrahydrofuran, 40 g of 2,3-dimethyl-2-butanol and 40.93 g of triethylamine under a N2 atmosphere. To this was dropwise added 40.927 g of purified methacroyl chloride from an addition funnel. Reaction was allowed to warm moderately. After 24 hrs of stirring, the tetrahydrofuran was roto-evaporated from the solution and 100 mL of ethyl acetate was added. The salts were then filtered off though a Buchner funnel. The ethyl acetate was then stripped by use of a rotory-evaporator. A vacuum distillation column was set up with an 8 inch Vigreaux column, stir bar and a few small boiling chips. A fractional distillation was performed and 19.8 g of the product was recovered in the fraction which had a boiling point of approximately 80-87° C. at 6-7 Torr of pressure. 1H NMR was used to confirm structure and purity.
Workup
- additionInto a 500 mL flask containing a stir bar
- customfitted with a condenser
- customReaction
- temperatureto warm moderately
- customthe tetrahydrofuran was roto-evaporated from the solution and 100 mL of ethyl acetate
- additionwas added
- filtrationThe salts were then filtered off though a Buchner funnel
- customThe ethyl acetate was then stripped by use of a rotory-evaporator
- distillationA vacuum distillation column
- stirringstir bar
- distillationA fractional distillation
- custom19.8 g of the product was recovered in the fraction which
Sources & evidence
- ORD record
- ord-e6e06b91ee8547f09a170c9381bc2265
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06379861B1
Reaction notes
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