N-methyl-2-pyrrolidone → HCID 90408140, compound

HRID 2275415Notes

Reaction equation

HRID 2275415 reaction equation
C([O:4][C:5]1[C:6]([CH3:20])=[C:7]([CH:17]=[CH:18][CH:19]=1)[C:8]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:9])C=C.CN1C[CH2:25][CH2:24][C:23]1=O>>[CH2:25]([C:19]1[CH:18]=[CH:17][C:7]([C:8]([O:10][CH2:11][CH2:12][Si:13]([CH3:14])([CH3:15])[CH3:16])=[O:9])=[C:6]([CH3:20])[C:5]=1[OH:4])[CH:24]=[CH2:23]

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 90408053HCID 90408053, compound

Product 1

HCID 90408140HCID 90408140, compound

Conditions

Temperature
220 °C

Procedure

2-(Trimethylsilyl)ethyl 3-(allyloxy)-2-methylbenzoate (500 mg, 1.70 mmol) was dissolved in 1-methylpyrrolidine-2-one (1 ml) in a microwave vial, closed with a cap and subjected to microwave irradiation (CEM discover) with stirring at 220° C., maximum pressure 300 psi, run time 5 min, hold time 15 min. LCMS showed 3 peaks including a major peak with the expected product mass. After cooling, the crude mixture was directly loaded on a silica gel column (12 g) and purified using an ISCO system (hexane:EtOAc solvent mixture, product eluted ˜5% EtOAc in hexane) to give SKC-01-056. The above experiment was repeated several times in 1-2 g scale Total wt of the product isolated was 3.6 g.

Workup

  1. customclosed with
  2. customa cap
  3. customsubjected to microwave irradiation (CEM discover)
  4. customtime 5 min
  5. customtime 15 min

Sources & evidence

ORD record
ord-6c673f2b3f8f480cbc09b520b6ac0de9
Source dataset
uspto-grants-2015_09
Patent number
US09127024B2

Reaction notes

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