1,2-Ethanedithiol → HCID 86674106, compound

HRID 1525145Notes

Reaction equation

HRID 1525145 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6][CH2:5]2.[CH2:13]([SH:16])[CH2:14][SH:15].[OH-].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]1([S:16][CH2:13][CH2:14][S:15]1)[CH2:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 109021,2-EthanedithiolHCID 14798Sodium HydroxideHCID 101050696-Bromo-1-tetralone

Product 1

HCID 86674106HCID 86674106, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-bromo-3,4-dihydro-2H-naphthalen-1-one (CAS[66361-67-9]) (0.9 g, 4.00 mmol) in dichloromethane (8 ml) was cooled to 0° C. and treated with 1,2-ethandithiol (769 mg, 686 μl, 8.00 mmol) and boron trifluoro etherate (284 mg, 247 μl, 2.00 mmol). The reaction mixture was left to warm to room temperature and stirred for 15 hours. For the workup, the reaction mixture was poured into a solution of sodium hydroxide (1N) followed by extraction with dichloromethane (40 ml). The organic layer was dried over sodium sulphate and evaporated. The crude product was purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 70:30 as the eluent. The 6′-bromo-3′,4′-dihydro-2′H-spiro[[1,3]dithiolane-2,1′-naphthalene] (1.06 g, 88% yield) was obtained as a light red oil.

Workup

  1. waitThe reaction mixture was left
  2. extractionfollowed by extraction with dichloromethane (40 ml)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated
  5. customThe crude product was purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 70:30 as the eluent

Sources & evidence

ORD record
ord-240a9f7f4406416caf05f748d424ddf8
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

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