Sodium borohydride → HCID 13808652, compound

HRID 652435Notes

Reaction equation

HRID 652435 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]1[S:11][C:10]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:9]=2[O:8][CH2:7][C:6]1=[O:18].[BH4-].[Na+]>O1CCCC1.CO>[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]1[S:11][C:10]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:9]=2[O:8][CH2:7][CH:6]1[OH:18]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 13808651HCID 13808651, compound

Product 1

HCID 13808652HCID 13808652, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-chloropropyl)-7-methoxy-3,4-dihydro-2H-1,5-benzoxathiepin-3-one (0.8 g) in tetrahydrofuran (2 ml) and methanol (10 ml) is added sodium borohydride (0.1 g) under ice-cooling. The reaction mixture is stirred for another one hour and evaporated in vacuo. The residue is mixed with ethyl acetate and water. The orgonic layer is separated, washed with water, dried over anhydrous sodium sulfate and evaporated to dryness in vacuo. The residue is submited to column chromatography on silica gel eluting with ethyl acetate-hexane (1:1) to give 4-(3-chloropropyl)-7-methoxy-3,4-dihydro-2H-1,5-benzoxathiepin-3-ol (0.68 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. customevaporated in vacuo
  3. additionThe residue is mixed with ethyl acetate and water
  4. customThe orgonic layer is separated
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-94988ebe73bc42a186ce17d5154ca02f
Source dataset
uspto-grants-1987_06
Patent number
US04672064

Reaction notes

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