Diethyl Ether → HCID 11596091, compound

HRID 1422311Notes

Reaction equation

HRID 1422311 reaction equation
[C:1]1([C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][CH:16]=[O:17])[N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].C(OCC)C>C(O)C.CO.ClCCl>[C:24]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[N:10]=[CH:9]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 11538160HCID 11538160, compound

Product 1

HCID 11596091HCID 11596091, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of the product from step c (16.1 g, 42.4 mmol) in ethanol (300 ml) was cooled under an atmosphere of argon to 0° C. Sodium borohydride (1.57 g, 42.4 mmol) was added, the mixture stirred for 4 h and carefully quenched with saturated ammonium chloride. The mixture was extracted with dichloromethane (3×100 ml). The combined extracts were dried over magnesium sulfate, filtered and evaporated to give a white solid, which was dissolved in a 5% methanol/dichloromethane and preciptated with diethyl ether. Thus, the product was isolated as a colourless crystalline solid (9.34 g, 58%).

Workup

  1. customcarefully quenched with saturated ammonium chloride
  2. extractionThe mixture was extracted with dichloromethane (3×100 ml)
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a white solid, which

Sources & evidence

ORD record
ord-9c2b50a50dd1404c9747bdcac6744be8
Source dataset
uspto-grants-2000_06
Patent number
US06080871

Reaction notes

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