Triethylamine → HCID 178496288, compound

HRID 1369192Notes

Reaction equation

HRID 1369192 reaction equation
[C:1]([C@@:4]12[CH2:13][CH2:12][CH2:11][CH2:10][C@:9]1([OH:14])[CH2:8][CH2:7][CH2:6][CH2:5]2)(=[O:3])[CH3:2].[CH3:15][O:16][CH2:17][CH2:18][O:19][CH2:20]Cl.C(N(CC)CC)C>C1COCC1>[C:1]([C@@:4]12[CH2:13][CH2:12][CH2:11][CH2:10][C@:9]1([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])[CH2:8][CH2:7][CH2:6][CH2:5]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 178465752HCID 178465752, compound

Product 1

HCID 178496288HCID 178496288, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 100 mmol of 4a-acetyl-8a-hydroxy-cis-decalin, 110 mmol of 2-methoxyethoxymethyl chloride, 110 mmol of triethylamine, and 200 ml of THF was refluxed for 3 hours. The resulting reaction mixture was subjected to column chromatography on a silica gel to yield 4a-acetyl-8a-(2-methoxyethoxymethoxy)-cis-decalin represented by the following formula (yield: 90.3%). The conversion rate from 4a-acetyl-8a-hydroxy-cis-decalin was 95%.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-4f4f8b63edec4110abbf797215b1fb2b
Source dataset
uspto-grants-2003_06
Patent number
US06576787B1

Reaction notes

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