Naphthalene → HCID 22850341, compound

HRID 1974779Notes

Reaction equation

HRID 1974779 reaction equation
CS(O[CH2:6][C:7]12[O:37][CH:8]1[C@@H:9]1[C@H:13]([CH2:14]2)[C@H:12](/[CH:15]=[CH:16]/[C@@H:17]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:11]([O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[CH2:10]1)(=O)=O.C1C2C(=CC=CC=2)C=CC=1.[Na].[Cl-].[NH4+]>O1CCCC1.CCCCCC.C(OCC)(=O)C>[OH:37][CH:8]1[C:7](=[CH2:6])[CH2:14][C@H:13]2[C@@H:9]1[CH2:10][C@@H:11]([O:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][O:32]1)[C@H:12]2/[CH:15]=[CH:16]/[C@@H:17]([O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 931NaphthaleneHCID 25517Ammonium Chloride2×HCID 5360545SodiumHCID 86747557HCID 86747557, compound

Product 1

HCID 22850341HCID 22850341, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A solution of the (1S,2RS,3RS,5S,6S,7R)-3-methanesulfonyloxymethyl-2,3-epoxy-6-[(E,3S)-3-(2-tetrahydropyranyloxy)-1-octenyl]-7-(2-tetrahydropyranyloxy) bicyclo[3.3.0]octane (781 mg, 1.40 mmoles) in 3 ml of tetrahydrofuran was added to an anion radical solution prepared by reacting naphthalene (1.28 g, 10 mmoles) and sodium (207 mg, 9 mmoles) in 30 ml of tetrahydrofuran at room temperature for 1 hour. The mixture was stirred at room temperature for 10 minutes. To the reaction solution was addded 3.0 g of ammonium chloride, and thereafter, a saturated aqueous solution of ammonium chloride was added. The mixture was worked up and extracted with ethyl acetate. The organic layer was washed with sodium chloride, dried over anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to column chromatography (silica gel 50 g; hexane/ethyl acetate=19/1) to give (1S,2RS,5S,6S,7R)-2-hydroxy-3-methylene-6-[(E,3S)-3-(2-tetrahydropyranyloxy)-1-octenyl]-7-(2-tetrahydropyranyloxy)bicyclo[3.3.0]octane (520 mg, 1.12 mmoles, 80%).

Workup

  1. customprepared
  2. customat room temperature
  3. customfor 1 hour
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto obtain a crude product

Sources & evidence

ORD record
ord-904dd753a9514a429b8321c859ee7f6b
Source dataset
uspto-grants-1994_02
Patent number
US05283349

Reaction notes

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