Hydrochloric Acid → HCID 23021551, compound

HRID 501813Notes

Reaction equation

HRID 501813 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][C:8]=1[O:16][CH3:17])[CH3:2].ClC(OCC)=O.[BH4-].[Na+].Cl>O1CCCC1.C(N(CC)CC)C.O.C(OCC)(=O)C>[OH:12][CH2:11][C:10]1[CH:14]=[CH:15][C:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:18])=[C:8]([O:16][CH3:17])[CH:9]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 23021533HCID 23021533, compound

Product 1

HCID 23021551HCID 23021551, compoundYield 99.8%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.58 g of 4-(3-ethoxy-3-oxopropyl)-3-methoxybenzoic acid was dissolved in 16 mL of tetrahydrofuran, to which 0.96 mL of triethylamine was added dropwise at −10° C. and then 0.63 mL of ethyl chloroformate was added dropwise at −20° C., followed by addition thereto of 0.47 g of sodium borohydride in an ice bath, and this solution was stirred for 30 minutes at the same temperature. The reaction mixture, to which water was added dropwise before adding ethyl acetate and water thereto, was adjusted to pH 2 with 6M hydrochloric acid, and the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure to yield 1.49 g of ethyl 3-[4-(hydroxymethyl)-2-methoxyphenyl]propanoate as white solid.

Workup

  1. additionwas added dropwise at −10° C.
  2. additionfollowed by addition
  3. customthe organic phase was separated
  4. washAfter the resultant organic phase was washed with water
  5. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-a653ff0974384a348a27d2a9f4986079
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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