Lithium borohydride → 5-Ethyl-6-(4-hydroxy-3-methyl-but-2-enyl)4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one

HRID 272199Notes

Reaction equation

HRID 272199 reaction equation
[CH2:1]([C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:4]=1[CH2:21][CH:22]=[C:23]([CH3:26])[CH:24]=[O:25])[CH3:2].[BH4-].[Li+]>CO.CO.O.C1COCC1>[CH2:1]([C:3]1[C:11]([CH3:12])=[C:10]2[C:6](=[C:5]([O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:19])[CH3:20])[C:4]=1[CH2:21][CH:22]=[C:23]([CH3:26])[CH2:24][OH:25])[C:7](=[O:13])[O:8][CH2:9]2)[CH3:2]

Participants

6

Reactant 2

HCID 4148881Lithium borohydrideHCID 725636044-[6-Ethyl-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enal

Product 1

HCID 670098805-Ethyl-6-(4-hydroxy-3-methyl-but-2-enyl)4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-oneYield 73.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

4-[6-Ethyl-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enal (77.6 mg, 0.207 mmol) was dissolved in MeOH (4 mL). A solution of CeCl3 (51.1 mg, 0.207 mmol) in MeOH/water (9/1, 0.66 mL) was added and the solution was cooled to 0° C. A solution of lithium borohydride in THF (2M, 0.105 mL) was added dropwise. After 15 minutes, the reaction was quenched with 1N HCl (0.5 mL). The MeOH was removed in vacuo and the crude material was partitioned between DCM and water. The aqueous layer was extracted with DCM and the combined organic layers were washed with sodium bicarbonate solution and dried over sodium sulfate. Filtration and evaporation of solvents yielded a crude oil, which was purified by silica gel chromatography to provide 57.2 mg (73%) of the desired product. 1H NMR (300 MHz, CDCl3): δ=0.04 (s, 9H), 1.15 (t, J=7.8 Hz, 3H), 1.26 (m, 2H), 1.86 (s, 3H), 2.19 (s, 3H), 2.72 (q, J=7.8 Hz, 2H), 3.52 (d, J=6.3 Hz, 2H), 3.99 (s, 2H), 4.34 (m, 2H), 5.14 (s, 2H), 5.32 (m, 1H) ppm.

Workup

  1. customthe reaction was quenched with 1N HCl (0.5 mL)
  2. customThe MeOH was removed in vacuo
  3. customthe crude material was partitioned between DCM and water
  4. extractionThe aqueous layer was extracted with DCM
  5. washthe combined organic layers were washed with sodium bicarbonate solution
  6. dry with materialdried over sodium sulfate
  7. filtrationFiltration and evaporation of solvents
  8. customyielded a crude oil, which
  9. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-0e18f85efcc64386bc6ff9e2a23d7f3e
Source dataset
uspto-grants-2008_11
Patent number
US07452901B2

Reaction notes

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