Pyridine → HCID 12251286, compound

HRID 596288Notes

Reaction equation

HRID 596288 reaction equation
[C:1]12([CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]1)[C:10]1[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:4][CH2:3][CH2:2]2.N1C=CC=CC=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>O>[CH3:23][S:24]([O:16][CH:13]1[CH2:12][CH2:11][C:1]2([C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)[CH2:15][CH2:14]1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 12251285HCID 12251285, compound

Product 1

HCID 12251286HCID 12251286, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice-cooled solution of 3.89 g. (0.018 M) of 3',4'-dihydrospiro[cyclohexane-1,1'(2'H)-naphthalen]-4-ol -(obtained in Example 17A) in 40 ml. of pyridine, 4 ml. of methane sulfonyl chloride is added. The mixture is allowed to stand in the cold for about 6 hours and then diluted with water. The material that precipitates is extracted with ether and the combined extracts washed successively with ice cold 2.5 N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and brine and then evaporated to dryness. The residue is recrystallized from cyclohexane to give 5 g. (94.3% yield) of 3',4'-dihydrospiro[cyclohexane-1,1'(2'H)-naphthalen]-4-ol methane sulfonate(t), having a melting point of 118° to 120° C.

Workup

  1. customcold for about 6 hours
  2. customThe material that precipitates
  3. extractionis extracted with ether
  4. washthe combined extracts washed successively with ice cold 2.5 N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and brine
  5. customevaporated to dryness
  6. customThe residue is recrystallized from cyclohexane
  7. customto give 5 g

Sources & evidence

ORD record
ord-9ddd81a7899049e395e92f6fcbe10ee0
Source dataset
uspto-grants-1977_03
Patent number
US04010201

Reaction notes

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