Triethylamine → HCID 178460453, compound

HRID 1369195Notes

Reaction equation

HRID 1369195 reaction equation
[C:1]([O:5][C:6]([C@@:9]12[CH2:18][CH2:17][CH2:16][CH2:15][C@:14]1([OH:19])[CH2:13][CH2:12][CH2:11][CH2:10]2)([CH3:8])[CH3:7])(=[O:4])[CH:2]=[CH2:3].[CH2:20]=[C:21]1[O:25][C:23](=[O:24])[CH2:22]1.C(N(CC)CC)C>O1CCCC1>[C:23]([O:19][C@@:14]12[CH2:15][CH2:16][CH2:17][CH2:18][C@:9]1([C:6]([O:5][C:1](=[O:4])[CH:2]=[CH2:3])([CH3:8])[CH3:7])[CH2:10][CH2:11][CH2:12][CH2:13]2)(=[O:24])[CH2:22][C:21]([CH3:20])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12661DiketeneHCID 178460452HCID 178460452, compound

Product 1

HCID 178460453HCID 178460453, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 100 mmol of 4a-(1-acryloyloxy-1-methylethyl)-8a-hydroxy-cis-decalin prepared in the same manner as in Example 4, 110 mmol of diketene, 110 mmol of triethylamine, and 300 ml of tetrahydrofuran was stirred at room temperature for 2 hours. The resulting reaction mixture was subjected to chromatography on a silica gel to yield 8a-acetoacetyloxy-4a-(1-acryloyloxy-1-methylethyl)-cis-decalin represented by the following formula (yield: 89.1%). The conversion rate from 4a-(1-acryloyloxy-1-methylethyl)-8a-hydroxy-cis-decalin was 99%.

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-f5eb2504b6b24902af9b3c2d5cb58440
Source dataset
uspto-grants-2003_06
Patent number
US06576787B1

Reaction notes

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