Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 86748310, compound

HRID 1492010Notes

Reaction equation

HRID 1492010 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:13][O:12][C@H:11]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C@@H:10]1[CH:20]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(P(=[CH:41][C:42]([O:44][CH3:45])=[O:43])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Si:1]([O:8][C@@H:9]1[CH2:13][O:12][C@H:11]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C@@H:10]1/[CH:20]=[CH:41]/[C:42]([O:44][CH3:45])=[O:43])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 57039924HCID 57039924, compound

Product 1

HCID 86748310HCID 86748310, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9.75 g (0.0292 mol) of (2S,3S,4S)-4-(t-butyldimethylsilyloxy)2-(3-pyridyl)tetrahydrofuran-3-carboxaldehyde in 120 ml of methylene chloride is added 9.75 g (0.0292 mol) of methyl (triphenylphosphoranylidene)acetate, the mixture is stirred at room temperature overnight and evaporated. The residue is triturated with ether to precipitate out most of the triphenylphosphine oxide, filtered and washed with ether. The filtrates are evaporated and the residue is purified by flash chromatography from silica gel (5×9 cm2) using methylene chloride-ethyl acetate (1:1) as eluent to give 6.77 g of methyl (E)-(2S,3S,4S)-3-[4-(t-butyldimethylsilyloxy)-2-(3-pyridyl)tetrahydrofuran-3-yl]-2-propenoate with elemental analysis: C, 62.67; H, 8.12; N, 3.86 (theory: C, 62.78, H, 8.04; N, 3.85) and optical rotation [α]D 25=+26.77 (8.9 mg/ml methanol).

Workup

  1. customevaporated
  2. customThe residue is triturated with ether
  3. customto precipitate out most of the triphenylphosphine oxide
  4. filtrationfiltered
  5. washwashed with ether
  6. customThe filtrates are evaporated
  7. customthe residue is purified by flash chromatography from silica gel (5×9 cm2)

Sources & evidence

ORD record
ord-fd9d331759fb48b8aadd26b544adf199
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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