Borane;tetrahydrofuran → HCID 69632012, compound

HRID 1358779Notes

Reaction equation

HRID 1358779 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:21](O)=[O:22])[CH:17]=2)[CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1>C1COCC1>[CH2:1]([O:8][C:9]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][OH:22])[CH:17]=2)[CH:12]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 19031950HCID 19031950, compound

Product 1

HCID 69632012HCID 69632012, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2,6-Naphthalenedicarboxylic acid monobenzyl ester (2.9 g, 9.5 mmol) in anhydrous THF (50 ml) under N2 at 0° C., was added 1.0M BH3.THF (14.3 ml, 14.3 mmol). The mixture was stirred at room temperature for overnight, then partitioned between brine (200 ml) and EtOAc (3×75), dried over Na2SO4, and taken to dryness to yield a white solid (6-Hydroxymethyl-2-naphthalenecarboxylic acid benzyl ester, 2.6 g). 1H NMR (360 MHz, DMSO-d6): δ 8.635 (s, 1H, Ar—H), 8.110 (d, J=8.6 Hz, 1H, Ar—H), 8.004 (m, 2H, Ar—H), 7.919 (s, 1H, Ar—H), 7.574-7.366 (m, 6H, Ar—H), 5.425-5.393 (m, 2H, —COOCH2—), 4.71-4.696(d, J=5.2 Hz, 2H, HO—CH2—), MS m/e 291 [M+−1].

Workup

  1. custompartitioned between brine (200 ml) and EtOAc (3×75)
  2. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-0789d8befff74a21a2684d86526d6a5e
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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