Hydrochloric Acid → HCID 18421128, compound

HRID 725292Notes

Reaction equation

HRID 725292 reaction equation
[OH:1][C:2]1[C:16]([OH:17])=[C:15]([OH:18])[C:5]2[C:6]3[CH2:7][CH2:8][CH2:9][C:10]=3[C:11](=[O:14])[CH2:12][CH2:13][C:4]=2[CH:3]=1.COB(OC)OC.[S:26](Cl)([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27].Cl>C(Cl)Cl.O1CCCC1.O.C(N(CC)CC)C>[OH:17][C:16]1[C:2]([O:1][S:26]([C:29]2[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=2)(=[O:28])=[O:27])=[CH:3][C:4]2[CH2:13][CH2:12][C:11](=[O:14])[C:10]3[CH2:9][CH2:8][CH2:7][C:6]=3[C:5]=2[C:15]=1[OH:18]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8470Trimethyl borateHCID 10131100HCID 10131100, compound

Product 1

HCID 18421128HCID 18421128, compoundYield 97.6%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

30 g of 2,3,5,6-tetrahydro-8,9,10-trihydroxy-benz[e]azulen-4(1H)-one obtained in Example 1, 300 ml of tetrahydrofuran, 60 ml of triethylamine and 12.9 ml of trimethylborate were stirred for 90 minutes at 20° C.±2° C. 30 g of tosyl chloride were added and the mixture was stirred for 16 hours at 20° C.±2° C. and then over 10 minutes at 20° C.±2° C., the reaction medium was poured into a stirred mixture of 900 ml of demineralized water and 150 ml of concentrated hydrochloric acid. Then, 90 ml of tetrahydrofuran and 60 ml of methylene chloride were added and the solution was stirred for one hour at 20° C. Then, 150 ml of methylene chloride were introduced and the mixture was stirred for 15 minutes, followed by decanting and extracting twice with 75 ml of methylene chloride. The combined organic phases were washed 4 times with 150 ml of demineralized water and reextracted with 75 ml of methylene chloride. After concentration under a reduced pressure of 20 mbars until distillation no longer occurred at 50° C., 47.6 g of the expected product were obtained.

Workup

  1. waitover 10 minutes at 20° C.±2° C.
  2. stirringthe solution was stirred for one hour at 20° C
  3. stirringthe mixture was stirred for 15 minutes
  4. customby decanting
  5. extractionextracting twice with 75 ml of methylene chloride
  6. washThe combined organic phases were washed 4 times with 150 ml of demineralized water
  7. concentrationAfter concentration under a reduced pressure of 20 mbars
  8. distillationuntil distillation
  9. customno longer occurred at 50° C.

Sources & evidence

ORD record
ord-5225adc2004d49b8958dcae76a0ce001
Source dataset
uspto-grants-1998_01
Patent number
US05705704

Reaction notes

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