Ethyl Acrylate → HCID 70276507, compound

HRID 1075555Notes

Reaction equation

HRID 1075555 reaction equation
[CH2:1]([O:3][C:4](=[O:7])[CH:5]=[CH2:6])[CH3:2].[C:8]([Si:12]([O:15][C@@H:16]1[C@H:25]2[C@@:20]([CH3:30])([C@@H:21]([C@H:26]([CH3:29])[CH2:27]I)[CH2:22][CH2:23][CH2:24]2)[CH2:19][CH2:18][CH2:17]1)([CH3:14])[CH3:13])([CH3:11])([CH3:10])[CH3:9]>N1C=CC=CC=1.O1CCCC1.[Zn]>[CH2:1]([O:3][C:4](=[O:7])[CH2:5][CH2:6][CH2:29][C@H:26]([C@@H:21]1[C@:20]2([CH3:30])[C@H:25]([C@@H:16]([O:15][Si:12]([C:8]([CH3:10])([CH3:9])[CH3:11])([CH3:14])[CH3:13])[CH2:17][CH2:18][CH2:19]2)[CH2:24][CH2:23][CH2:22]1)[CH3:27])[CH3:2]

Participants

5

Reactant 2

HCID 8821Ethyl AcrylateHCID 70273115HCID 70273115, compound

Product 1

HCID 70276507HCID 70276507, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 16069498Pyridine tetrahydrofuranSolvent2×

Procedure

To 342.5 mg (5.24 mMol) of Zn powder are added 1.57 ml of tetrahydrofuran/pyridine 2/1. The reaction mixture is stirred under Argon, 247.2 mg (1.04 mMol) of NiCl2.6H2O and then 472.2 mg (4.72 mMol) of ethylacrylate are added. The reaction mixture is heated at 65° for 30 minutes, cooled to room temperature and 947 mg (2.10 mMol) of (1S,4aR,5R,8aR)-tert-Butyl[5-[(S)-2-iodo-1-methyl-ethyl]-4a-methyl-decahydronaphtalen-1-yloxy]-dimethylsilane dissolved in 1.57 ml of tetrahydrofuran pyridine 1/2 are added and the reaction mixture kept overnight at room temperature. Filtration through Speedex and washing of the filter cake with ethylacetate is followed by evaporation in vacuo to 1/3 of the volume. The solution is diluted with ethylacetate and the organic phase is washed 4 times with a disodium ethylene diamine tetraacetate dihydrate (EDTA) solution (8 g of EDTA and 8 g of NaHCO3 in 100 ml water) and twice with brine. The organic phase is dried over Na2SO4, filtered and evaporated in vacuo. The residue is chromatographed over 100 g of silicagel with hexane/ethylacetate 98/2 to yield 269 mg of starting material and 390 mg (44%) of (R)-5-[(1R,4aR,5S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphtalen-1-yl)-hexanoic acid ethyl ester as an amorphous product.

Workup

  1. temperatureThe reaction mixture is heated at 65° for 30 minutes
  2. additionare added
  3. filtrationFiltration through Speedex
  4. washwashing of the filter cake with ethylacetate
  5. customis followed by evaporation in vacuo to 1/3 of the volume
  6. additionThe solution is diluted with ethylacetate
  7. washthe organic phase is washed 4 times with a disodium ethylene diamine tetraacetate dihydrate (EDTA) solution (8 g of EDTA and 8 g of NaHCO3 in 100 ml water)
  8. dry with materialThe organic phase is dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe residue is chromatographed over 100 g of silicagel with hexane/ethylacetate 98/2

Sources & evidence

ORD record
ord-13c26126de104e05b704453eddc15587
Source dataset
uspto-grants-1999_05
Patent number
US05905074

Reaction notes

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