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Acetic Acid → Ethyl 4,5,6,7-tetramethoxy-2-[4-(4-methoxycarbonylphenoxy)butyl]-1-oxo-2-indancarboxylate

HRID 2268464
Notes
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Reaction equation

HRID 2268464 reaction equation
C([Li])CCC.Br[C:7]1[C:12]([CH2:13][C:14]([C:35](OCC)=O)([CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:11]([O:40][CH3:41])[C:10]([O:42][CH3:43])=[C:9]([O:44][CH3:45])[C:8]=1[O:46][CH3:47].C(O)(=[O:50])C.C(=O)(O)[O-].[Na+]>C1COCC1.CCCCCC>[CH3:41][O:40][C:11]1[C:10]([O:42][CH3:43])=[C:9]([O:44][CH3:45])[C:8]([O:46][CH3:47])=[C:7]2[C:12]=1[CH2:13][C:14]([CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=1)([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:35]2=[O:50]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 18348654Ethyl 2-(6-bromo-2,3,4,5-tetramethoxybenzyl)-2-ethoxycarbonyl-6-(4-methoxycarbonylphenoxy)hexanoateHCID 178418339Butyllithium

Product 1

HCID 18348656Ethyl 4,5,6,7-tetramethoxy-2-[4-(4-methoxycarbonylphenoxy)butyl]-1-oxo-2-indancarboxylateYield 50.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A hexane solution of n-butyl lithium (1.68 M, 3.27 ml, 5.50 mmols) was dropwise added to a THF (30 ml) solution of ethyl 2-(6-bromo-2,3,4,5-tetramethoxybenzyl)-2-ethoxycarbonyl-6-(4-methoxycarbonylphenoxy)hexanoate (3.00 g, 4.58 mmols), under a nitrogen stream at −90° C. or lower, and stirring was continued for 15 minutes. Then, the temperature was raised to −78° C., and stirring was further continued for 15 minutes. To the reaction mixtures was added a THF (5 ml) solution of acetic acid (1.38 g, 22.9 mmols) at −70° C. or lower, which was then allowed to warm to room temperature, and a saturated aqueous sodium bicarbonate solution was added thereto, which was then extracted with diethyl ether. The organic layer waswashed with water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out, and the resulting crude product was purified by recrystallization (from hexane-ethyl acetate) to obtain the entitled compound (1.22 g) as crystals.

Workup

  1. stirringstirring
  2. waitwas further continued for 15 minutes
  3. customTo the reaction mixtures
  4. temperatureto warm to room temperature
  5. extractionwhich was then extracted with diethyl ether
  6. dry with materiala saturated aqueous sodium chloride solution, and then dried
  7. customThe solvent was evaporated out
  8. customthe resulting crude product was purified by recrystallization (from hexane-ethyl acetate)

Sources & evidence

ORD record
ord-6651d75278e14a9b98ca46da7429ee17
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06326369B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes