Ethyl isobutyrate → ethyl (E)-6-(1,3-dihydro-4-methoxyethoxymethoxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2,2,4-trimethyl-3-hydroxy-4-hexenoate

HRID 1781530Notes

Reaction equation

HRID 1781530 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[C:13]([O:18][CH2:19][CH3:20])(=[O:17])[CH:14]([CH3:16])[CH3:15].[CH3:21][O:22][C:23]1[C:31]([CH3:32])=[C:30]2[C:26]([C:27](=[O:33])[O:28][CH2:29]2)=[C:25]([O:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH3:40])[C:24]=1[CH2:41]/[CH:42]=[C:43](\[CH3:46])/[CH:44]=[O:45].[NH4+].[Cl-]>C1COCC1>[CH3:40][O:39][CH2:38][CH2:37][O:36][CH2:35][O:34][C:25]1[C:24]([CH2:41]/[CH:42]=[C:43](\[CH3:46])/[CH:44]([OH:45])[C:14]([CH3:16])([CH3:15])[C:13]([O:18][CH2:19][CH3:20])=[O:17])=[C:23]([O:22][CH3:21])[C:31]([CH3:32])=[C:30]2[C:26]=1[C:27](=[O:33])[O:28][CH2:29]2

Participants

7

Reactant 5

HCID 7342Ethyl isobutyrateHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 88264149(E)-4-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2-methylbut-2-enaldehydeHCID 178418339Butyllithium

Product 1

HCID 131720025ethyl (E)-6-(1,3-dihydro-4-methoxyethoxymethoxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2,2,4-trimethyl-3-hydroxy-4-hexenoateYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Freshly distilled diisopropylamine (0.425 ml) was dissolved in anhydrous THF (10 ml) and cooled to 0° C. n-BuLi (0.63 ml, 2.35M) was added slowly and the reaction was stirred at 0° C. for 20 minutes and cooled to -78°. Ethyl isobutyrate (0.200 ml) was added and the resulting solution was stirred at -78° C. for 40 minutes. A solution of (E)-4-(1,3-dihydro-6-methoxy -4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl) -2-methylbut-2-enaldehyde (365 mg) in THF (10 ml) was added and stirred for 30 min. The reaction mixture was poured to a concentrated solution of NH4Cl, and extracted with ethyl acetate (3×30 ml), the organic layers were dried over Na2SO4, and evaporated to give 420 mg (87%) of ethyl (E)-6-(1,3-dihydro-4-methoxyethoxymethoxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl) -2,2,4-trimethyl-3-hydroxy-4-hexenoate as an oil.

Workup

  1. additionwas added slowly
  2. temperaturecooled to -78°
  3. stirringthe resulting solution was stirred at -78° C. for 40 minutes
  4. stirringstirred for 30 min
  5. extractionextracted with ethyl acetate (3×30 ml)
  6. dry with materialthe organic layers were dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-5345bf2b94bc498b82d222f982316189
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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