Acetone → HCID 13316994, compound

HRID 325540Notes

Reaction equation

HRID 325540 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=2/[CH:16]=[CH:17]/[C@H:18]2[O:23][CH:22]([O:24]CC)[CH2:21][C@H:20]([OH:27])[CH2:19]2)=[CH:4][C:3]=1[CH3:28].CC(C)=O.[OH-].[Na+]>C(O)(=O)C.O.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=2/[CH:16]=[CH:17]/[C@H:18]2[O:23][CH:22]([OH:24])[CH2:21][C@H:20]([OH:27])[CH2:19]2)=[CH:4][C:3]=1[CH3:28]

Participants

7

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 13316992HCID 13316992, compound

Product 1

HCID 13316994HCID 13316994, compoundYield 48.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of the crude mixture of anomers, (4R,6S)-(E)-6-[2-(4'-fluoro-3,3',5-trimethyl[1,1'-biphenyl]-2-yl)ethenyl]-2-ethoxy-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran (0.83 g, 0.0021 mole) in glacial acetic acid (36 ml) was added water (12 ml). Additional acetic acid (3 ml) was added and the solution allowed to stand for 24 hours at which time tlc (silica gel, 5% acetone--CH2Cl2) indicated the reaction was essentially complete. The reaction mixture was poured into water (800 ml) containing sodium hydroxide (50 g) and extracted with ether (1200 ml). After washing the ether extract with water, drying (MgSO4) and evaporating there was obtained crude lactol product (0.68 g). The crude product was purified by flash chromatography (45 mm id column, 4% acetone --CH2Cl2) to give 0.36 g of product which showed a single spot on tlc. 360 MHz H' -NMR in DCCl3 confirmed the presence of two hydroxy anomers in the product.

Workup

  1. extractionextracted with ether (1200 ml)
  2. washAfter washing the ether
  3. extractionextract with water
  4. dry with materialdrying (MgSO4)
  5. customevaporating there
  6. customwas obtained crude lactol product (0.68 g)
  7. customThe crude product was purified by flash chromatography (45 mm id column, 4% acetone --CH2Cl2)

Sources & evidence

ORD record
ord-3d184dfda9764382bcf71c63a18d9783
Source dataset
uspto-grants-1984_04
Patent number
US04440927

Reaction notes

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