Borane;tetrahydrofuran → 2-(4-Hydroxymethyl-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester

HRID 709484

Reaction equation

HRID 709484 reaction equation
[Cl:1][C:2]([Cl:25])([Cl:24])[CH2:3][O:4][C:5](=[O:23])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](O)=[O:21])=[CH:16][CH:15]=1.B.C1COCC1>C1COCC1>[Cl:25][C:2]([Cl:1])([Cl:24])[CH2:3][O:4][C:5](=[O:23])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 668652432-(4-Carboxy-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester

Product 1

HCID 668652542-(4-Hydroxymethyl-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(4-Carboxy-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester (80 mg, 0.191 mmol) in THF (1 mL) at 0° C. was added dropwise BH3-THF (0.4 mL, 1.0M solution in THF). The reaction was stirred at 0° C. for 0.5 h after the addition was complete, thereafter the cooling bath was removed and the reaction was stirred for 2 h at rt. The reaction was quenched at 0° C. by careful addition of THF/H2O, 80/20 followed by dropwise addition of 2M HCl. The mixture was stirred for an additional 10 minutes and thereafter diluted with water. THF was removed and the water phase was extracted with DCM and the combined organic phase was dried through a phase separator and concentrated to give the titled compound (70 mg, 91%) as an oil; 1H NMR (400 MHz, CDCl3): δ 4.53 (s, 2H), 4.64 (s, 2H), 4.94 (s, 2H), 7.19-7.30 (m, 5H), 7.30-7.36 (m, 1H), 7.37-7.44 (m, 1H), 8.06 (d, 1H).

Workup

  1. additionafter the addition
  2. customthe cooling bath was removed
  3. stirringthe reaction was stirred for 2 h at rt
  4. customThe reaction was quenched at 0° C. by careful addition of THF/H2O, 80/20
  5. additionfollowed by dropwise addition of 2M HCl
  6. stirringThe mixture was stirred for an additional 10 minutes
  7. additiondiluted with water
  8. customTHF was removed
  9. extractionthe water phase was extracted with DCM
  10. customthe combined organic phase was dried through a phase separator
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-1917137476da45608302e5ee2555c87b
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Linked notes

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