Potassium Bromide → HCID 86662610, compound

HRID 1404725Notes

Reaction equation

HRID 1404725 reaction equation
[C:1]([C:3]([CH3:12])([CH2:9][S:10][CH3:11])[C:4]([O:6]CC)=[O:5])#[N:2].[K+].[Br-]>CO>[C:1]([C:3]([CH3:12])([CH2:9][S:10][CH3:11])[C:4]([OH:6])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 86662609HCID 86662609, compound

Product 1

HCID 86662610HCID 86662610, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-cyano-2-methyl-3-methylsulfanyl-propanoate (2.3 g, 12.3 mmol) was added to ice-cold sodium hydroxide (5 mL, 2N) under stirring. Methanol (10 mL) was added and the ice bath removed after an hour. After 45 minutes at room temperature, volatiles were removed under reduced pressure and the residue diluted with water (20 mL). Impurities were removed by ether extraction (2×30 mL). The aqueous layer was cooled in ice, acidified to pH 3 with dilute HCl and extracted with ethyl acetate (3×30 mL). Combined organic extracts were dried over MgSO4 and concentrated under reduced pressure to leave a brown gum. Yield 1.32 g (68%): IR (KBr thin film) 1735 cm−1; 1H NMR (400 MHz, CDCl3) δ 10.19 (br, 1H), 3.10 (d, J=14.2 Hz, 1H), 2.94 (d, J=13.9 Hz, 1H), 2.33 (s, 3H), 1.73 (s, 3H); 13C NMR (400 MHz, CDCl3) δ 173.33, 118.82, 45.86, 41.66, 23.05, 17.62.

Workup

  1. customthe ice bath removed after an hour
  2. customvolatiles were removed under reduced pressure
  3. additionthe residue diluted with water (20 mL)
  4. customImpurities were removed by ether extraction (2×30 mL)
  5. temperatureThe aqueous layer was cooled in ice
  6. extractionextracted with ethyl acetate (3×30 mL)
  7. dry with materialCombined organic extracts were dried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customto leave a brown gum

Sources & evidence

ORD record
ord-42b6762afe0c4512afa050be07da8f71
Source dataset
uspto-grants-2014_12
Patent number
US08912338B2

Reaction notes

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