Acetic Anhydride → HCID 23320340, compound

HRID 1155494Notes

Reaction equation

HRID 1155494 reaction equation
[OH:1][C:2]1([CH2:20][OH:21])[CH2:11][C:10]2[C:5](=[C:6]([O:14][CH3:15])[CH:7]=[CH:8][C:9]=2[O:12][CH3:13])[C:4]2([S:19][CH2:18][CH2:17][S:16]2)[CH2:3]1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>N1C=CC=CC=1>[C:22]([O:21][CH2:20][C:2]1([OH:1])[CH2:11][C:10]2[C:5](=[C:6]([O:14][CH3:15])[CH:7]=[CH:8][C:9]=2[O:12][CH3:13])[C:4]2([S:16][CH2:17][CH2:18][S:19]2)[CH2:3]1)(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13264151HCID 13264151, compound

Product 1

HCID 23320340HCID 23320340, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.6 g of rac-1',2',3',4'-tetrahydro-3'-hydroxy-3'-hydroxymethyl-5',8'-dimethoxyspiro[1,3-dithiolane-2,1'-naphthalene] were dissolved in 30 ml of dry pyridine and 1.5 g of acetic anhydride were added to the solution. The mixture was left to stand at room temperature for 20 hours and then poured into ice-cold 5-M sulphuric acid. The resulting mixture was extracted with ethyl acetate, the extracts were washed with water and sodium hydrogen carbonate solution, dried and evaporated to give 1.8 g of rac-3'-acetoxymethyl-1',2',3',4'-tetrahydro-3'-hydroxy-5',8'-dimethoxyspiro[1,3-dithiolane-2,1'-naphthalene] in the form of a colourless oil which was used directly in the next step.

Workup

  1. waitThe mixture was left
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washthe extracts were washed with water and sodium hydrogen carbonate solution
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-c3d597250b2a4ea19c0be8e47acb9914
Source dataset
uspto-grants-1981_11
Patent number
US04302398

Reaction notes

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