Trifluoroacetic acid → HCID 21700327, compound

HRID 1085639Notes

Reaction equation

HRID 1085639 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].OCCS(C1C(OCCC)=C(OC)C=C([C@@H:19]([OH:36])[CH2:20][CH2:21][CH:22]([C:24]2[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=2)O)C=1)(=O)=O.FC(F)(F)C(O)=O.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C(Cl)(Cl)Cl>[CH3:31][O:30][C:28]1[CH:29]=[C:24]([CH:22]2[O:36][CH2:19][CH2:20][CH2:21]2)[CH:25]=[C:26]([O:34][CH3:35])[C:27]=1[O:32][CH3:33]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 15718042HCID 15718042, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21700327HCID 21700327, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the more mobile fraction of 1-(5-(2-hydroxyethylsulfonyl)-4-n-propoxy-3-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl-4-oxo-butan-1-yl(R)-(O)-methylmandelate (200 mg, 0.300 mmole) in dry THF (15 mL) at 0° C. under nitrogen atmosphere was treated with lithium aluminum hydride (20 mg, 0.5 mmole), and stirred for 2 hours. After the usual workup, the crude (1S, 4RS)-1-(5-(2-hydroxyethylsulfonyl)-4-n-propoxy-3-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-butan-1,4-diol was dissolved in chloroform (2 mL, stabilized with ethanol), chilled to 0° C., stirred, and treated with 10% (v/v) of trifluoroacetic acid in chloroform (2 mL, stabilized with ethanol). After 4 hours at 0° C., anhydrous Na2CO3 (1.0 mg, 9.4 mmole) was added, and the mixture was stirred for additional 15 minutes. The mixture was then filtered, and the filtrate was evaporated to a syrup which was purified by preparative TLC SiO2 plates developed with 3:2 (v/v) ethyl acetate hexane to provide (-)-(2S,5S)-2-(5-2-hydroxyethylsulfonyl)-4-n-propoxy-3-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-tetrahydrofuran, m.p. 111°-112° C.; [α]D -61.4° (c=1, CHCl3).

Workup

  1. stirringstirred
  2. waitAfter 4 hours at 0° C.
  3. stirringthe mixture was stirred for additional 15 minutes
  4. filtrationThe mixture was then filtered
  5. customthe filtrate was evaporated to a syrup which
  6. customwas purified by preparative TLC SiO2 plates

Sources & evidence

ORD record
ord-e631e010b28e41efbed8c635de571b5d
Source dataset
uspto-grants-1991_04
Patent number
US05010100

Reaction notes

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