Sodium borohydride → HCID 13808652, compound

HRID 580074Notes

Reaction equation

HRID 580074 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-823186b7384844049abdf98d5b73d959
Source dataset
uspto-grants-1988_06
Patent number
US04751316

Reaction notes

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