3-Methyl-isothiazole → HCID 59556170, compound

HRID 1173293Notes

Reaction equation

HRID 1173293 reaction equation
C([Li])CCC.[CH3:6][C:7]1[CH:11]=[CH:10][S:9][N:8]=1.[O:12]1[C:16]2([CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)[O:15][CH2:14][CH2:13]1>CCCCCC.O1CCCC1>[CH3:6][C:7]1[CH:11]=[C:10]([C:19]2([OH:22])[CH2:20][CH2:21][C:16]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:17][CH2:18]2)[S:9][N:8]=1

Participants

6

Reactant 3

HCID 127473-Methyl-isothiazoleHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418339Butyllithium

Product 1

HCID 59556170HCID 59556170, compoundYield 70.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

At −78° C., 1.5 M of n-butyllithium in hexane (6.7 mL) was slowly added to a solution of 3-methylisothiazole (1.0 g, 0.010 mol) in tetrahydrofuran (15 mL) over a period of 20 min. After being stirred for another 30 min, 1,4-dioxa-spiro[4.5]decan-8-one (1.56 g, 0.00999 mol) in tetrahydrofuran (5 mL) was added within 10 min. The reaction mixture was stirred for another 2 hour at −78° C. and allowed to warm up overnight to room temperature. After quenching with with brine, the mixture was extracted with EtOAc. The organic layer was dried and concentrated. Chromatography on silica gel eluting with hexane/EtOAc (1:5˜1:1) provided 1.8 g (70.6%) of the title compound. MS (M+H)+ 256.

Workup

  1. stirringThe reaction mixture was stirred for another 2 hour at −78° C.
  2. temperatureto warm up overnight to room temperature
  3. customAfter quenching with with brine
  4. extractionthe mixture was extracted with EtOAc
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-872cf27573a2466597170ba95b68f55d
Source dataset
uspto-grants-2010_11
Patent number
US07834021B2

Reaction notes

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