Water → 7-(Methylsulfanyl)-9H-xanthene-3-carbaldehyde

HRID 1199726Notes

Reaction equation

HRID 1199726 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][S:8][C:9]1[CH:22]=[CH:21][C:20]2[O:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:23][OH:24])[CH:17]=3)[CH2:12][C:11]=2[CH:10]=1.C(N(CC)CC)C.O>C(Cl)Cl.CS(C)=O.C(OCC)(=O)C>[CH3:7][S:8][C:9]1[CH:22]=[CH:21][C:20]2[O:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH:23]=[O:24])[CH:17]=3)[CH2:12][C:11]=2[CH:10]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19865558[7-(Methylsulfanyl)-9H-xanthen-3-yl]methanol

Product 1

HCID 198655577-(Methylsulfanyl)-9H-xanthene-3-carbaldehyde

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under dry nitrogen, dimethylsulphoxide (5 ml) was added dropwise to a stirred solution of oxalyl chloride (0.89 ml) in methylene chloride (5 ml) at -60° C. After 2 minutes a solution of the xanthene from step (A) (2.3 g) in dimethylsulphoxide (35 ml) was introduced dropwise over 5 minutes whilst maintaining the temperature below -50° C. with cooling. After 15 minutes triethylamine (6.20 ml) was added, the mixture allowed to warm to room temperature and then poured into water. The mixture was ethyl acetate extracted, the organic layers were combined, washed with brine, dried over magnesium sulphate and evaporated yielding the title carboxaldehyde (1.97 g), m.p. 122°-123° C.

Workup

  1. temperaturewhilst maintaining the temperature below -50° C.
  2. temperaturewith cooling
  3. extractionextracted
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customyielding the title carboxaldehyde (1.97 g), m.p. 122°-123° C.

Sources & evidence

ORD record
ord-010d55eb04834467b77a1d56a9e94278
Source dataset
uspto-grants-1990_02
Patent number
US04902701

Reaction notes

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