Sodium borohydride → HCID 15078335, compound

HRID 1110835Notes

Reaction equation

HRID 1110835 reaction equation
[BH4-].[Na+].[OH:3][CH2:4][CH2:5][S:6]([C:9]1[CH:10]=[C:11]([C:27](=[O:44])[CH2:28][CH2:29][C:30]([C:32]2[CH:37]=[C:36]([O:38][CH3:39])[C:35]([O:40][CH3:41])=[C:34]([O:42][CH3:43])[CH:33]=2)=[O:31])[CH:12]=[C:13]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:14]=1[O:15][CH2:16][CH2:17][CH3:18])(=[O:8])=[O:7]>C(O)C.ClCCl>[OH:3][CH2:4][CH2:5][S:6]([C:9]1[CH:10]=[C:11]([CH:27]([OH:44])[CH2:28][CH2:29][CH:30]([C:32]2[CH:33]=[C:34]([O:42][CH3:43])[C:35]([O:40][CH3:41])=[C:36]([O:38][CH3:39])[CH:37]=2)[OH:31])[CH:12]=[C:13]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:14]=1[O:15][CH2:16][CH2:17][CH3:18])(=[O:8])=[O:7]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 15078285HCID 15078285, compound

Product 1

HCID 15078335HCID 15078335, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

Sodium borohydride (0.66 g) was added to a suspension of 1-[3-(2-hydroxyethylsulfonyl)-4-propoxy-5-benzyloxyphenyl]-4-(3,4,5-trimethoxyphenyl) butan-1,4-dione (from previous experiment) in ethanol (125 mL), and the mixture was heated at 75° C. for 2 h. The solution was cooled and diluted with dichloromethane. It was then washed with 2.5 N HCl (2 x) and water, dried, and evaporated to a syrup, Rf 0.11 (hexane-ethyl acetate., 1:1, v/v). This material was used directly in the next experiment without further purification.

Workup

  1. temperatureThe solution was cooled
  2. washIt was then washed with 2.5 N HCl (2 x) and water
  3. customdried
  4. customevaporated to a syrup, Rf 0.11 (hexane-ethyl acetate
  5. customThis material was used directly in the next experiment without further purification

Sources & evidence

ORD record
ord-9a7bd5a8820c4e23b9c8a09ac7fec3e2
Source dataset
uspto-grants-1990_12
Patent number
US04977146

Reaction notes

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