Dichloromethane → HCID 18594876, compound

HRID 2071338Notes

Reaction equation

HRID 2071338 reaction equation
[OH:1][CH:2]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][CH2:4][C@@H:5]1[C@@H:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8](=[O:21])[CH2:7][CH2:6]1.C(Cl)Cl.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(N(CC)CC)C>[CH3:30][S:31]([O:1][CH:2]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][CH2:4][C@@H:5]1[C@@H:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8](=[O:21])[CH2:7][CH2:6]1)(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 1859466215-Hydroxy-9-oxoprostanoic acid, ethyl ester

Product 1

HCID 18594876HCID 18594876, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 2.48 g. of ethyl 15-hydroxy-9-oxo-prostanoate (Example 50) in 18 ml. of methylene chloride containing 1.4 ml. of triethylamine, cooled in an ice-salt bath is added dropwise 0.58 ml. of methanesulfonyl chloride. The resulting mixture is stirred for 15 minutes and is then washed successively with ice cold water, 10% hydrochloric acid, saturated sodium bicarbonate solution, and saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness to give 2.7 g. (90%) of oil; λmax. 5.78 (carbonyl groups), 7.45 and 8.55 μ (sulfonate).

Workup

  1. additionis added dropwise 0.58 ml
  2. washis then washed successively with ice cold water, 10% hydrochloric acid, saturated sodium bicarbonate solution, and saturated sodium chloride solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customto give 2.7 g

Sources & evidence

ORD record
ord-063801f82868428b96afaa2db8d4f3ae
Source dataset
uspto-grants-1977_09
Patent number
US04046787

Reaction notes

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