Hydrochloric Acid → HCID 54469704, compound

HRID 443643Notes

Reaction equation

HRID 443643 reaction equation
[C:1]1([O:11][CH:12]([CH3:27])[C:13]([NH:15][C:16]2[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=2)=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.B#B.Cl>O1CCCC1>[C:1]1([O:11][CH:12]([CH3:27])[CH2:13][NH:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6328200DiboronHCID 17650482HCID 17650482, compound

Product 1

HCID 54469704HCID 54469704, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 8.29 g. ethyl 4-[2-(1-naphthyloxy)propionamido]benzoate in 75 ml. tetrahydrofuran is reacted with 34 ml. 1 M diborane in tetrahydrofuran. After stirring at room temperature for 5 days, the solution is poured into 750 ml. 5% HCl, stirred for about 1/2 hour until foaming stopped, and extracted three times with 250 ml. portions of methylene chloride. The combined extracts are washed with 200 ml. brine, dried and condensed to nearly colorless oil. Crystallization from acetonitrile yield white solid, m.p. 110°-111.5° C.

Workup

  1. additionthe solution is poured into 750 ml
  2. extractionextracted three times with 250 ml
  3. washThe combined extracts are washed with 200 ml
  4. dry with materialbrine, dried
  5. customcondensed to nearly colorless oil
  6. customCrystallization from acetonitrile
  7. customyield white solid, m.p. 110°-111.5° C.

Sources & evidence

ORD record
ord-98d1fb0ff5f14266a23c0501f98f690d
Source dataset
uspto-grants-1981_04
Patent number
US04260816

Reaction notes

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