Water → HCID 20500929, compound

HRID 2164467Notes

Reaction equation

HRID 2164467 reaction equation
O[CH2:2][CH2:3][CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])=[CH:5]1.[CH2:21](N(CC)CC)C.S(Cl)(C)(=O)=O.[OH2:33]>C(Cl)Cl>[OH:33][CH2:21][CH2:2][CH2:3][CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])=[CH:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13229104HCID 13229104, compound

Product 1

HCID 20500929HCID 20500929, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 17.2 g of 3-(2-hydroxy ethyl) 3,4-dihydro 1-orthofluorophenyl naphthalene [(IV), n=2] obtained in example 11 above in 200 ml of methylene chloride, cooled to -10° C., are added 22.3 ml of triethylamine then 10 ml of mesyl chloride. It is left at -10° C., and when the reaction is finished (checked by T.L.C.), it is diluted with water, washed with a dilute hydrochloric solution, then with water, then with a dilute sodium bicarbonate solution, then with water, dried on magnesium sulfate, filtered and the filtrate is evaporated. The crude product (22.2 g) is dissolved in 100 ml of DMSO and 25 g of sodium cyanide are added. The mixture is left for a night at ambient temperature, then diluted with water, extracted with chloroform, washed with water, dried on magnesium sulfate, filtered and the filtrate is evaporated. 18 g of the expected product (oily) are obtained.

Workup

  1. waitIt is left at -10° C.
  2. washwashed with a dilute hydrochloric solution
  3. dry with materialwith water, then with a dilute sodium bicarbonate solution, then with water, dried on magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate is evaporated
  6. dissolutionThe crude product (22.2 g) is dissolved in 100 ml of DMSO
  7. addition25 g of sodium cyanide are added
  8. waitThe mixture is left for a night at ambient temperature
  9. additiondiluted with water
  10. extractionextracted with chloroform
  11. washwashed with water
  12. customdried on magnesium sulfate
  13. filtrationfiltered
  14. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-c3533f84face45e7b0b694b900c3f113
Source dataset
uspto-grants-1985_03
Patent number
US04504663

Reaction notes

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