Tetrahydrofuran → Ethyl 4-(1-hydroxy-2-methylpropyl)benzoate

HRID 1820976Notes

Reaction equation

HRID 1820976 reaction equation
I[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH:13]([Mg]Cl)(C)C.[CH2:18]1C[O:21][CH2:20][CH2:19]1>>[OH:21][CH:20]([C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1)[CH:19]([CH3:18])[CH3:13]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 142891Ethyl 4-iodobenzoateHCID 178418918HCID 178418918, compound

Product 1

HCID 68853898Ethyl 4-(1-hydroxy-2-methylpropyl)benzoate

Conditions

Temperature
-40 °C

Procedure

To a solution of 3.19 g (11.6 mmol) of ethyl 4-iodobenzoate in 10 mL of THF at −40° C. was added 6.4 mL (12.7 mmol) of isopropylmagnesium chloride (2.0 M in THF). After stirring at −40° C. for 1 h, 1.26 mL (13.9 mmol) of isobutylaldehyde was added. After stirring at −40° C. for 1 h, the reaction was quenched by adding 10 mL of saturated NaHCO3. The mixture was warmed to rt and poured into brine (20 mL). The aqueous layer was extracted with CH2Cl2 (3×20 mL). Organic layers were combined, dried over Na2SO4, and concentrated. Chromatography on a Biotage 40M cartridge using 1:9 v/v EtOAc/hexanes as the eluant gave 2.08 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 0.82 (d, J=6.9, 3H), 0.96 (d, J=6.6, 3H), 1.39 (t, J=7.1, 3H), 1.95 (m, 1H), 2.09 (br. s, 1H), 4.36 (q, J=7.1, 2H), 4.45 (d, J=6.4, 1H), 7.37 (d, J=8.2, 2H), 7.99 (d, J=8.3, 2H).

Workup

  1. stirringAfter stirring at −40° C. for 1 h
  2. customthe reaction was quenched
  3. additionby adding 10 mL of saturated NaHCO3
  4. temperatureThe mixture was warmed to rt
  5. additionpoured into brine (20 mL)
  6. extractionThe aqueous layer was extracted with CH2Cl2 (3×20 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2530c0533ea64c6ea4cfeb0117b3d03b
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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