Chloride → HCID 14537110, compound

HRID 232402Notes

Reaction equation

HRID 232402 reaction equation
[Cl-].CS(C)=O.[CH3:6][O:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[C:10]([CH2:25][CH2:26][CH2:27][OH:28])[CH:9]=1.C(N(CC)CC)C>C(Cl)Cl>[CH:27]([CH2:26][CH2:25][C:10]1[CH:9]=[C:8]([O:7][CH3:6])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1)=[O:28]

Participants

6

Reactant 4

HCID 312ChlorideHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 14537109HCID 14537109, compound

Product 1

HCID 14537110HCID 14537110, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

An oven-dried 25 ml 2-necked (14/20) round bottom flask, equipped with magnetic stirring bar, nitrogen inlet and serum cap, is charged with a solution of oxalkyl chloride (61 μl) in 2 ml methylene chloride. This solution is placed under a nitrogen atmosphere and cooled to -60° C. to -50° C. Dimethylsulfoxide (99 μl) is added (neat) dropwise to give a colorless solution. After 2-3 min a solution of 3-[4-methoxy-1-[(tetrahydro-2H-pyran-2-yl)oxy]-2-naphthalenyl]-1-propanol (0.19 g) in 1 ml methylene chloride is added drowpise. The resulting mixture is stirred at -60° C. to -50° C. for 15 min and then treated with triethylamine (0.44 ml). This gives rise to a yellow colored milky suspension. The cooling bath is removed and the stirred mixture is allowed to warm to room temperature at which time the mixture is diluted with water and extracted with ether. The organic phase is washed three times with water (after adjusting the pH to 7 with 10% aqueous sodium bisulfate), dried with magnesium sulfate, filtered and concentrated to give 0.18 g of the crude title compound as an orange colored oil.

Workup

  1. customserum cap
  2. temperaturecooled to -60° C. to -50° C
  3. customto give a colorless solution
  4. customThe cooling bath is removed
  5. additionis diluted with water
  6. extractionextracted with ether
  7. washThe organic phase is washed three times with water (
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-a1c08ca23d8b4518b04208ab25dd95e8
Source dataset
uspto-grants-1989_07
Patent number
US04851586

Reaction notes

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