Triethylamine → 2-[6-(2-Benzyloxyacetoxy)naphthalen-2-yl]propionic acid methyl ester

HRID 638759Notes

Reaction equation

HRID 638759 reaction equation
[CH2:1]([O:8][CH2:9][C:10](Cl)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:13][O:14][C:15](=[O:29])[CH:16]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([OH:28])[CH:24]=2)[CH:19]=1)[CH3:17].C(N(CC)CC)C>CC(C)=O>[CH3:13][O:14][C:15](=[O:29])[CH:16]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:28][C:10](=[O:11])[CH2:9][O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:24]=2)[CH:19]=1)[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 177085Benzyloxyacetyl chlorideHCID 5988972-(6-Hydroxy-naphthalen-2-yl)-propionic acid methyl ester

Product 1

HCID 592539682-[6-(2-Benzyloxyacetoxy)naphthalen-2-yl]propionic acid methyl esterYield 63.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzyloxy acetyl chloride (24 gm, 86.95 mmol) was added drop-wise to a mixture of 2-(6-Hydroxynaphthalen-2-yl)-propionic acid methyl ester 6 (20 g, 86.95 mmol) and triethylamine (22.5 g, 222.35 mmol) in acetone (300 ml) and stirred for 2 hrs at room temp. Solids were filtered off, acetone distilled off, and water (100 ml) added. Crude 99 was extracted into chloroform, washed with 5% sodium bicarbonate (2×50 ml), water (2×50 ml), dried over sodium sulphate and distilled. Crude 99 was purified by recrystallising in chloroform:hexane (1:6) to get pure 99 (21 g, 63.9%) as a white powder. M.p: 58-60° C.

Workup

  1. filtrationSolids were filtered off
  2. distillationacetone distilled off
  3. additionwater (100 ml) added
  4. extractionCrude 99 was extracted into chloroform
  5. washwashed with 5% sodium bicarbonate (2×50 ml), water (2×50 ml)
  6. dry with materialdried over sodium sulphate
  7. distillationdistilled
  8. customCrude 99 was purified
  9. customby recrystallising in chloroform:hexane (1:6)

Sources & evidence

ORD record
ord-b889b1a3d7314ea183a6f0d14413f00a
Source dataset
uspto-grants-2010_04
Patent number
US07691364B2

Reaction notes

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