Methyl iodide → HCID 118062422, compound

HRID 920729Notes

Reaction equation

HRID 920729 reaction equation
[OH:1][CH2:2][C:3]([CH3:10])([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].C1CCN2C(=NCCC2)CC1.[C:22](=[S:24])=[S:23].[CH3:25]I>CN(C=O)C>[CH3:9][C:3]([CH3:10])([CH2:2][O:1][C:22]([S:24][CH3:25])=[S:23])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 274432ethyl 3-hydroxy-2,2-dimethylpropanoate

Product 1

HCID 118062422HCID 118062422, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethyl 3-hydroxy-2,2-dimethylpropanoate (3.0 g, 20.52 mmol) in DMF (15 mL) was added DBU (3.10 g, 20.52 mmol) at RT followed by slow addition of CS2 (3.12 g, 41.0 mmol) over a period of 10 minutes. The reaction mixture was stirred at RT for 30 min, and then cooled to 10° C. prior to addition of MeI (6.58 mL, 103 mmol). The reaction mixture was stirred for 2 h at RT after which it was quenched with ice water and extracted with diethyl ether (2×25 mL). The combined organic layer was dried over Na2SO4, filtered and the filtrate evaporated to afford Intermediate 212A as a pale yellow liquid (3.0 g, 62%). 1H NMR (300 MHz, chloroform-d) δ ppm 4.59 (s, 2H), 4.19 (q, J=7.05 Hz, 2H), 2.55 (s, 3H), 1.23-1.29 (m, 9H).

Workup

  1. temperaturecooled to 10° C.
  2. stirringThe reaction mixture was stirred for 2 h at RT after which it
  3. customwas quenched with ice water
  4. extractionextracted with diethyl ether (2×25 mL)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customthe filtrate evaporated

Sources & evidence

ORD record
ord-4330452f89384e76b21d16f3a34421a1
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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