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Diethyl Ether → HCID 22821307, compound

HRID 67738
Notes
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Reaction equation

HRID 67738 reaction equation
C([Li])CCC.C[C:7](C)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:8][C:9](=[O:15])[CH2:10]P(=O)([O-])[O-].CCOCC.[CH:28]([C@H:30]1[C@H:37]([O:38][C:39](=[O:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:36][C@H:35]2[C@@H:31]1[CH2:32][C:33](=[O:47])[O:34]2)=O>CCCCCC.C(O)(=O)C.O1CCCC1>[O:15]=[C:9]([CH2:8][CH2:7][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)/[CH:10]=[CH:28]/[C@H:30]1[C@H:37]([O:38][C:39](=[O:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:36][C@H:35]2[C@@H:31]1[CH2:32][C:33](=[O:47])[O:34]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 3283Diethyl Ether2×HCID 11000244(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoateHCID 53442789Dimethyl-2-oxo-4-phenylbutylphosphonateHCID 178418339Butyllithium

Product 1

HCID 22821307HCID 22821307, compound

Reagents, catalysts & solvents 3

HCID 176
Acetic Acid
Solvent
HCID 8028TetrahydrofuranSolvent
HCID 8058HexaneSolvent

Procedure

At 20° under argon, 20 ml. of a 2-molar butyllithium solution in hexane was added dropwise to a solution of 11.2 g. of dimethyl-2-oxo-4-phenylbutylphosphonate in 400 ml. of ether. The mixture was stirred for 5 minutes and then 600 ml. of ether was added thereto and the mixture again stirred for 5 minutes at 20°. Thereafter, a solution of 9.26 g. of (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3,3,0]octan-3-one [J. Amer. Chem. Soc. 96, 5865 (1974)] in 150 ml. of tetrahydrofuran was added dropwise to this mixture, and the latter was agitated for 30 minutes at 20°. 6 ml. of glacial acetic acid was added thereto, and the mixture was evaporated under vacuum. The residue was taken up in 600 ml. of methylene chloride, shaken twice with respectively 100 ml. of saturated sodium bicarbonate solution, twice with respectively 100 ml. of water, dried over magnesium sulfate, and evaporated under vacuum. After recrystallization from isopropyl ether/methylene chloride, 11 g. of the title compound was obtained as colorless crystals; m.p. 119°-120°.

Workup

  1. customAt 20°
  2. stirringthe mixture again stirred for 5 minutes at 20°
  3. stirringthe latter was agitated for 30 minutes at 20°
  4. customthe mixture was evaporated under vacuum
  5. stirringof methylene chloride, shaken twice with respectively 100 ml
  6. dry with materialof water, dried over magnesium sulfate
  7. customevaporated under vacuum
  8. customAfter recrystallization from isopropyl ether/methylene chloride, 11 g

Sources & evidence

ORD record
ord-5b290b7740b4424bbd16e3567573194c
Source dataset
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04346228

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes