Boron Trichloride → Acetic acid 7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl ester

HRID 643903Notes

Reaction equation

HRID 643903 reaction equation
B(Cl)(Cl)Cl.C[O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][CH:13]([O:17][C:18](=[O:20])[CH3:19])[CH2:14]2)=[CH:9][CH:8]=1>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].C(Cl)Cl>[OH:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][CH:13]([O:17][C:18](=[O:20])[CH3:19])[CH2:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 25135Boron TrichlorideHCID 66750527HCID 66750527, compound

Product 1

HCID 66750587Acetic acid 7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl ester

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

BCl3 (1 M in DCM, 56 mL) is added to a mixture of acetic acid 7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl ester (4.94 g, 22.5 mmol) and Bu4NI (10.8 g, 29.2 mmol) in DCM (112 mL) at −78° C. The mixture is stirred at −78° C. and then warmed to room temperature over 1 h. The mixture is partitioned between EtOAc and ice-cold brine. The organic layer is dried over MgSO4, concentrated and chromatographed to afford acetic acid 7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl ester as a yellow oil, which upon standing at room temperature becomes a solid: 1H NMR (CDCl3) δ 6.96 (d, J=8.0 Hz, 1H), 6.64 (d, J=8.0 Hz, 1H), 6.55 (s, 1H), 5.18 (m, 1H), 5.00 (m, 1H), 3.05 (dd, J=16.0, 8.0 Hz, 1H), 2.90-2.72 (m, 3H), 2.06 (s, 3H), 2.06-1.89 (m, 2H).

Workup

  1. temperaturewarmed to room temperature over 1 h
  2. customThe mixture is partitioned between EtOAc and ice-cold brine
  3. dry with materialThe organic layer is dried over MgSO4
  4. concentrationconcentrated
  5. customchromatographed

Sources & evidence

ORD record
ord-e7837363cb424d8d94ce9d16c9cabb09
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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