Ethyl Acetate → 3-Methyl-3-(thiocyanatomethyl)oxetane

HRID 1259410Notes

Reaction equation

HRID 1259410 reaction equation
[C:1]([S-:3])#[N:2].[K+].CC1C=CC(S(O[CH2:16][C:17]2([CH3:21])[CH2:20][O:19][CH2:18]2)(=O)=O)=CC=1.C(OCC)(=O)C>C(O)C.CCCCCC>[CH3:16][C:17]1([CH2:21][S:3][C:1]#[N:2])[CH2:20][O:19][CH2:18]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 516872Potassium thiocyanateHCID 5461213(3-Methyloxetan-3-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 579302753-Methyl-3-(thiocyanatomethyl)oxetaneYield 304.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Conditions

Temperature
85 °C

Procedure

KSCN (0.75 g, 7.81 mmol) was added to a solution of (3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate (1 g, 3.90 mmol) in ethanol (25 mL) and the resulting reaction mass was heated at 85° C. overnight. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mass was concentrated under reduced pressure to afford 1.7 g of the crude product which was used for the next step without further purification.

Workup

  1. customthe resulting reaction mass
  2. concentrationThe reaction mass was concentrated under reduced pressure

Sources & evidence

ORD record
ord-55025f7d748b4896a907e070ca9e6e41
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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