Tetrahydrofuran → HCID 59093773, compound

HRID 2181606Notes

Reaction equation

HRID 2181606 reaction equation
[BH4-].[Na+].C1COCC1.[CH:8]([C:10]1[Se:11][C:12]([C:15]2[Se:16][C:17]([C:20]3[Se:21][C:22]([CH:25]=[O:26])=[CH:23][CH:24]=3)=[CH:18][CH:19]=2)=[CH:13][CH:14]=1)=[O:9]>C(OCC)(=O)C>[OH:26][CH2:25][C:22]1[Se:21][C:20]([C:17]2[Se:16][C:15]([C:12]3[Se:11][C:10]([CH2:8][OH:9])=[CH:14][CH:13]=3)=[CH:19][CH:18]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 59093769HCID 59093769, compound

Product 1

HCID 59093773HCID 59093773, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

NaBH4 (10 mg) was added to a THF solution (2 mL) containing 2,5″-diformyl-5,2′:5′,2″-terselenophene (15 mg) and stirred at room temperature for 5 h. The reaction solution was diluted with ethyl acetate (50 mL), washed with 2N HCl (5 mL), and washed with H2O (3×100 mL). The organic layer was separated, dried over MgSO4, filtered, and the solvent was removed under vacuum. The residue was chromatographed over silica gel using (1:1) hexanes/ethyl acetate to afford 2,5″-dihydroxymethyl-5,2′:5′,2″-terselenophene in 98% yield.

Workup

  1. washwashed with 2N HCl (5 mL)
  2. washwashed with H2O (3×100 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed under vacuum
  7. customThe residue was chromatographed over silica gel using (1:1) hexanes/ethyl acetate

Sources & evidence

ORD record
ord-36bdeb8561c24252832daf84162e2ec9
Source dataset
uspto-grants-2005_05
Patent number
US06894039B2

Reaction notes

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