Hydrochloric Acid → (r/s)-2-(6-(2,3-Dihydro-1h-inden-2-yloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)acetic acid

HRID 731186Notes

Reaction equation

HRID 731186 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]([CH2:21][C:22]([O:24]CC)=[O:23])[CH2:16][CH2:15][CH2:14]2.[Li+].[OH-].Cl>C1COCC1.O>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]([CH2:21][C:22]([OH:24])=[O:23])[CH2:16][CH2:15][CH2:14]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57835728(R/S) Ethyl 2-(6-(2,3-dihydro-1H-inden-2-yloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)acetate

Product 1

HCID 57835721(r/s)-2-(6-(2,3-Dihydro-1h-inden-2-yloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of (R/S)-ethyl 2-(6-(2,3-dihydro-1H-inden-2-yloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)acetate 52 (85 mg, 0.24 mmol) and LiOH (40 mg) in THF-H2O (1/1, 4 mL) was stirred at room temperature for 6 hours. 2N HCl was added to acidify the mixture to pH 2-3. The mixture was then extracted with EtOAc (2×20 mL). The combined organic layers were washed with water and brine, and dried over Na2SO4. The residue obtained after filtration and concentration was purified with flash chromatography (0-60% EtOAc in hexane). (R/S)-2-(6-(2,3-Dihydro-1H-inden-2-yloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)acetic acid (53) was obtained as colorless oil (79 mg, 96%). MS ESI (neg.) m/e: 321 (M−H). 1H NMR (500 MHz) (CDCl3) δ 7.11-7.28 (m, 5H); 6.65-6.75 (m, 2H); 5.16 (m, 1H); 3.36-3.40 (m, 3H); 3.19 (dd, J=16.6, 3.0 Hz, 2H); 2.62-2.80 (m, 3H), 2.59 (q, J=9.9 Hz, 1H), 1.99 (m, 1H), 1.78-1.87 (m, 3H).

Workup

  1. extractionThe mixture was then extracted with EtOAc (2×20 mL)
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customThe residue obtained
  5. filtrationafter filtration and concentration
  6. customwas purified with flash chromatography (0-60% EtOAc in hexane)

Sources & evidence

ORD record
ord-922cd8fbd1cf48ec976a166cd7452bd0
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

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