Hydrochloric Acid → HCID 20389995, compound

HRID 839168Notes

Reaction equation

HRID 839168 reaction equation
B.[CH3:2][O:3][C:4]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:5]=1[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Br:13])=[O:7].Cl>O1CCCC1>[Br:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH:6]([C:5]1[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:4]=1[O:3][CH3:2])[OH:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 20389973HCID 20389973, compound

Product 1

HCID 20389995HCID 20389995, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Borane in tetrahydrofuran (240 ml. of 1M) was added over a period of 15 minutes to a solution of 72 g. of 5-(2-methoxy-4-chlorobenzoyl)pentyl bromide in 240 ml. of tetrahydrofuran. The mixture was stirred 45 minutes in an ice bath, and then 300 ml. of 2N hydrochloric acid was cautiously added. The mixture was concentrated to a volume of 500 ml., extracted with ether, the ether extracts washed with sodium bicarbonate and dried over anhydrous magnesium sulfate. Evaporation of the solvent afforded 74 g. of oil used in the next reaction without further purification.

Workup

  1. concentrationThe mixture was concentrated to a volume of 500 ml
  2. extraction, extracted with ether
  3. washthe ether extracts washed with sodium bicarbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent
  6. customafforded 74 g
  7. customof oil used in the next reaction without further purification

Sources & evidence

ORD record
ord-acdd7a173486443f8790fc68330ffa53
Source dataset
uspto-grants-1978_06
Patent number
US04093736

Reaction notes

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