Hydrochloric Acid → 7-(1-Methylethyl)-1,4-dioxa-8-thiaspiro[4.5]decane

HRID 656044Notes

Reaction equation

HRID 656044 reaction equation
ClN1[C:6](=[O:7])[CH2:5]CC1=O.[CH:9]12[S:16][CH:13]([CH2:14][CH2:15]1)[CH2:12][C:11](=[O:17])[CH2:10]2.[CH:18]([Mg]Br)(C)C.Cl>C1C=CC=CC=1.CCOCC>[CH3:18][CH:14]([CH:13]1[S:16][CH2:9][CH2:10][C:11]2([O:17][CH2:5][CH2:6][O:7]2)[CH2:12]1)[CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 2750548-Thiabicyclo(3.2.1)octan-3-oneHCID 178418365HCID 178418365, compound

Product 1

HCID 593327327-(1-Methylethyl)-1,4-dioxa-8-thiaspiro[4.5]decaneYield 65.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

N-Chlorosuccinimide (14.0 g, 104.9 mmol) was added in three portions with stirring over 15 min to a cooled (0° C.) solution of 8-thiabicyclo[3.2.1]octan-3-one (16.0 g, 99.9 mmol) in dry benzene (400 mL) under nitrogen. The mixture was stirred for a further 2.5 h and was then filtered. The filtrate was added dropwise with stirring under nitrogen to a cooled (0° C.) solution of isopropylmagnesium bromide (from isopropyl bromide (28.3 g, 229.7 mmol), magnesium (5.7 g, 234.7 mmol) and CuI (1.52 g, 7.9 mmol)) in dry ether (300 mL). The mixture was stirred for a further 15 h and cold (0° C.), dilute hydrochloric acid was added cautiously. The organic layer was separated and washed successively with water, saturated aqueous sodium bicarbonate, and finally with water again. The dried (Na2SO4) ether-benzene solution was evaporated, giving 13.2 g of the title compound.

Workup

  1. stirringThe mixture was stirred for a further 2.5 h
  2. filtrationwas then filtered
  3. additionThe filtrate was added dropwise
  4. stirringwith stirring under nitrogen to
  5. stirringThe mixture was stirred for a further 15 h
  6. customThe organic layer was separated
  7. washwashed successively with water, saturated aqueous sodium bicarbonate
  8. dry with materialThe dried (Na2SO4) ether-benzene solution
  9. customwas evaporated

Sources & evidence

ORD record
ord-b38c29a8b1ff41b5925e7ba996d83f2d
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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