Dichloromethane → HCID 22809232, compound

HRID 2052413Notes

Reaction equation

HRID 2052413 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15]([CH2:16][C@@H:17]([OH:27])[CH2:18][CH2:19]2)=[CH:14][CH2:13]3)[CH2:10][CH2:9]1)[CH3:7].C(N(C(C)C)CC)(C)C.[CH3:38][O:39][CH2:40][CH2:41][O:42][CH2:43]Cl.C(Cl)Cl>CCCCC>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15]([CH2:16][C@@H:17]([O:27][CH2:38][O:39][CH2:40][CH2:41][O:42][CH3:43])[CH2:18][CH2:19]2)=[CH:14][CH2:13]3)[CH2:10][CH2:9]1)[CH3:7]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 11153463CHOL-5-EN-24-oic acid, 3-hydroxy-, methyl ester, (3beta)-

Product 1

HCID 22809232HCID 22809232, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

A 100 ml round bottom flask, equipped with a mercury relief valve and magnetic stirrer, was flame-dried and flushed with nitrogen. The flask was charged with 2.57 mmoles (1.0 g) of 3β-hydroxy-5-cholenic acid methyl ester, 3.86 mmoles (0.50 g) of diisopropylethylamine, 3.86 mmoles (0.48 g) of methoxyethoxymethyl chloride and 10 ml of CH2Cl2. The reaction mixture was stirred for 48 hours at room temperature. After stirring, the reaction mixture was diluted with 25 ml of pentane, washed with 20 ml of 10% acetic acid and 20 ml of saturated sodium bicarbonate. The combined aqueous layers were extracted with two twenty ml portions of ether and the organic layers separated and dried with MgSO4. Concentration of the ether solution left an oily crude product (96%) which was isolated as a pure white solid (84%) by dissolving the oil in pentane, cooling to -78° C., and filtering. The pure solid had mp 44°-46° C.

Workup

  1. customA 100 ml round bottom flask, equipped with a mercury relief valve and magnetic stirrer
  2. customwas flame-dried
  3. customflushed with nitrogen
  4. stirringAfter stirring
  5. washwashed with 20 ml of 10% acetic acid and 20 ml of saturated sodium bicarbonate
  6. extractionThe combined aqueous layers were extracted with two twenty ml portions of ether
  7. customthe organic layers separated
  8. dry with materialdried with MgSO4
  9. waitConcentration of the ether solution left an oily crude product (96%) which

Sources & evidence

ORD record
ord-9c015e05cfa24caeaee675094cc09098
Source dataset
uspto-grants-1980_01
Patent number
US04183852

Reaction notes

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