Acetic Anhydride → HCID 23320340, compound

HRID 462633Notes

Reaction equation

HRID 462633 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-ef75915464db46f595e22962b2d7a28f
Source dataset
uspto-grants-1985_05
Patent number
US04515969

Reaction notes

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