HCID 86761589, compound → HCID 67229388, compound

HRID 1515783Notes

Reaction equation

HRID 1515783 reaction equation
C(S[C:4](=[O:20])[CH:5]([CH:11]1[CH2:19][CH2:18][C:13]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:12]1)C(SCC)=O)C>C1C=CC=CC=1.[Ni]>[O:14]1[C:13]2([CH2:18][CH2:19][CH:11]([CH2:5][CH2:4][OH:20])[CH2:12]2)[O:17][CH2:16][CH2:15]1

Participants

4

Reactant 1

HCID 86761589HCID 86761589, compound

Product 1

HCID 67229388HCID 67229388, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 241BenzeneSolvent2×

Procedure

To a solution Raney-Ni (250 mL) in benzene (100 mL) was added a solution of 2-(1,4-dioxa-spiro[4.4]non-7-yl)-dithiomalonic acid di-S-ethyl ester (28.7 g, 90 mmol) in benzene (600 mL). The mixture was stirred for 16 h at room temperature under nitrogen. The mixture was filtered to remove Raney-Ni and the filtrate was concentrated in vacuo. Purification by flash column chromatography (QingDao silica gel, 200-300 mesh, 5% ethyl acetate/pentane) afforded 2-(1,4-dioxa-spiro[4.4]non-7-yl)-ethanol (7 g, 45%).

Workup

  1. filtrationThe mixture was filtered
  2. customto remove Raney-Ni
  3. concentrationthe filtrate was concentrated in vacuo
  4. customPurification by flash column chromatography (QingDao silica gel, 200-300 mesh, 5% ethyl acetate/pentane)

Sources & evidence

ORD record
ord-ef63efd5f1e84902915551fbae9e3193
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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