Hydrochloric Acid → HCID 18980428, compound

HRID 2392767Notes

Reaction equation

HRID 2392767 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].[Na+].[CH:14]1(COS(C2C=CC(C)=CC=2)(=O)=O)[CH2:18]C[CH2:16][CH2:15]1.Cl.C(=O)([O-])O.[Na+]>CN(C)C=O.C(OC(C)C)(C)C.O>[CH:2]1([CH2:3][O:4][CH:5]2[CH2:6][CH2:7][C:8](=[O:11])[CH2:9][CH2:10]2)[CH2:16][CH2:15][CH2:14][CH2:18]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 5673521,4-Dioxaspiro(4.5)decan-8-olHCID 12568544Cyclopentylmethyl 4-methylbenzene-1-sulfonate

Product 1

HCID 18980428HCID 18980428, compoundYield 59.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 7914Diisopropyl EtherSolvent

Procedure

23.7 g (150 mmole) 1,4-dioxa-spiro[4.5]decan-8-ol were dissolved in 120 ml dimethylformamide and stirred for 1 hour in a nitrogen atmosphere at room temperature with 7.2 g (159 mmole) of 50% sodium hydride in mineral oil. 38 g (150 mmole) toluene-4-sulphonic acid cyclopentylmethyl ester were then added (Krapcho, Johnson, J. Org. Chem., 36, 146, (1971). The mixture was stirred at room temperature and cooled to a temperature between 5° C. and 10° C. 125 ml water were then added dropwise. The product was extracted with ether and dried over sodium sulphate, and the solvent was removed by distillation. The product obtained (32 g) was dissolved in diisopropyl ether and stirred for 20 hours with 65 ml water and 95 ml concentrated hydrochloric acid. It was then neutralised with sodium hydrogen carbonate, extracted with ether and dried over sodium sulphate. The oil obtained (23.4 g) was purified with 1:1 diisopropyl ether/n-hexane via a silica gel column. 17.5 g of compound (61) were obtained (60% theoretical).

Workup

  1. temperaturecooled to a temperature between 5° C. and 10° C
  2. extractionThe product was extracted with ether
  3. dry with materialdried over sodium sulphate
  4. customthe solvent was removed by distillation
  5. customThe product obtained (32 g)
  6. extractionextracted with ether
  7. dry with materialdried over sodium sulphate
  8. customThe oil obtained (23.4 g)
  9. customwas purified with 1:1 diisopropyl ether/n-hexane via a silica gel column

Sources & evidence

ORD record
ord-81964aece2f941d59d3e0093ad1757b7
Source dataset
uspto-grants-1998_09
Patent number
US05801201

Reaction notes

Loading…