Dimethyl Sulfide → HCID 54570347, compound

HRID 1438945Notes

Reaction equation

HRID 1438945 reaction equation
[CH3:1]SC.ClN1[C:9](=[O:10])[CH2:8][CH2:7][C:6]1=O.[CH3:12][O:13][C:14]([C:16]1(C2C=C(CO)C=CC=2)[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=2)[CH2:18][CH2:17]1)=[O:15].C(N([CH2:40][CH3:41])CC)C>C1(C)C=CC=CC=1>[CH3:12][O:13][C:14]([CH:16]1[C:24]2[C:19](=[CH:20][C:21]([C:9](=[O:10])[C:8]3[CH:41]=[CH:40][CH:1]=[CH:6][CH:7]=3)=[C:22]([O:25][CH3:26])[CH:23]=2)[CH2:18][CH2:17]1)=[O:15]

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 54051185HCID 54051185, compound

Product 1

HCID 54570347HCID 54570347, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

With stirring, 6 ml of dimethyl sulphide are added at 0° C in an atmosphere of nitrogen to a suspension of 8.05 g of N-chlorosuccinimide in 200 ml of absolute toluene and then at -25° C a solution of 12 g of crude 5-hydroxymethylphenyl-6-methoxy-indane-1-carboxylic acid methyl ester in 50 ml of absolute toluene is added. Upon completion of the addition, the mixture is further stirred for 90 minutes at -25° C. Then 8.3 ml of triethylamine are added to the reaction solution, which is stirred for a further 5 minutes and partitioned between 2 × 100 ml of 2 normal hydrochloric acid and 2 × 100 ml of ether. The organic phases are washed neutral, dried over sodium sulphate and evaporated to dryness in vacuo. The residue is chromatographed on silica gel with methylene chloride as eluant to yield 5-benzoyl-6-methoxy-indane-1-carboxylic acid methyl ester.

Workup

  1. additionUpon completion of the addition
  2. stirringthe mixture is further stirred for 90 minutes at -25° C
  3. stirringis stirred for a further 5 minutes
  4. custompartitioned between 2 × 100 ml of 2 normal hydrochloric acid and 2 × 100 ml of ether
  5. washThe organic phases are washed neutral
  6. dry with materialdried over sodium sulphate
  7. customevaporated to dryness in vacuo
  8. customThe residue is chromatographed on silica gel with methylene chloride as eluant

Sources & evidence

ORD record
ord-f6231d8ba23240e4b101b57b466a103b
Source dataset
uspto-grants-1977_11
Patent number
US04057573

Reaction notes

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