2-Naphthalenesulfonyl chloride → HCID 86747114, compound

HRID 2254650Notes

Reaction equation

HRID 2254650 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11](Cl)(=[O:13])=[O:12].[CH3:15][C:16]1([CH3:23])[O:20][C@@H:19]([CH2:21][OH:22])[CH2:18][O:17]1.C(N(CC)CC)C.C(OCC)(=O)C>O>[CH3:15][C:16]1([CH3:23])[O:20][C@@H:19]([CH2:21][O:22][S:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)(=[O:13])=[O:12])[CH2:18][O:17]1

Participants

6

Reactant 4

HCID 71252-Naphthalenesulfonyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 736057(+)-Solketal

Product 1

HCID 86747114HCID 86747114, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 53 parts of 2-naphthalenesulfonyl chloride, 30 parts of (S)-2,2-dimethyl-1,3-dioxolane-4-methanol, 70 parts of N,N-diethylethanamine and 180 parts of ethyl acetate was stirred for 2 hours at room temperature. The reaction mixture was poured into water and the product was extracted with methylbenzene. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromotography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated, yielding 62.8 parts (85.8%) of (R)-[(2,2-dimethyl-1,3-dioxolan-4-yl)-methyl]2-naphthalenesulfonate (interm. 9).

Workup

  1. extractionthe product was extracted with methylbenzene
  2. washThe extract was washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromotography over silica gel
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated

Sources & evidence

ORD record
ord-8548b7898e734954a90322537965ffae
Source dataset
uspto-grants-1993_08
Patent number
US05236944

Reaction notes

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