Acetic Anhydride → HCID 20337449, compound

HRID 1706254Notes

Reaction equation

HRID 1706254 reaction equation
[OH:1][C:2]1[C:19]([CH:20]([CH3:30])[CH2:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:18][C:5]2[O:6][C:7]([CH3:17])([CH3:16])[C:8]3[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][OH:15])[C:9]=3[C:4]=2[CH:3]=1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>C(#N)C>[C:31]([O:15][CH2:14][CH:10]1[C:9]2[C:4]3[CH:3]=[C:2]([OH:1])[C:19]([CH:20]([CH3:30])[CH2:21][CH2:22][CH2:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:18][C:5]=3[O:6][C:7]([CH3:16])([CH3:17])[C:8]=2[CH2:13][CH2:12][CH2:11]1)(=[O:33])[CH3:32]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 20337473HCID 20337473, compound

Product 1

HCID 20337449HCID 20337449, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.1 mole of dl-7,8,9,10-tetrahydro-2-hydroxy-10-hydroxymethyl-6,6-dimethyl-3-(1-methyl-4-phenylbutyl)-6H-dibenzo[b,d]pyran in 100 ml. of acetonitrile is treated with 0.1 mole of acetic anhydride and the mixture heated for 12 hours under nitrogen. It is then poured onto ice/water and extracted with ethyl acetate (2×100 ml.), the extracts combined, washed with brine and dried MgSO4). Evaporation under reduced pressure followed by silica gel chromatography affords the title product.

Workup

  1. temperaturethe mixture heated for 12 hours under nitrogen
  2. additionIt is then poured onto ice/water
  3. extractionextracted with ethyl acetate (2×100 ml.)
  4. washwashed with brine and dried MgSO4)
  5. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-ac3796004216476ba96a68131d7cc75f
Source dataset
uspto-grants-1980_06
Patent number
US04206225

Reaction notes

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