Sodium borohydride → 2-({6-[3-(1-Hydroxypentyl)-1-benzofuran-2-yl]-1-methyl-2-naphthyl}oxy)acetonitrile

HRID 1359226Notes

Reaction equation

HRID 1359226 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=4[C:16]=3[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:27][CH2:28][C:29]#[N:30].[BH4-].[Na+]>C(O)C>[OH:22][CH:17]([C:16]1[C:15]2[CH:23]=[CH:24][CH:25]=[CH:26][C:14]=2[O:13][C:12]=1[C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([CH3:1])=[C:3]([O:27][CH2:28][C:29]#[N:30])[CH:4]=[CH:5]2)[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 181828012-{[1-Methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile

Product 1

HCID 181828092-({6-[3-(1-Hydroxypentyl)-1-benzofuran-2-yl]-1-methyl-2-naphthyl}oxy)acetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the procedure described in Step 1 of Example 11, 2-{[1-methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile (0.874 g, 2.20 mmol) was reduced with sodium borohydride (0.495 g, 13.1 mmol) in ethanol (25 mL). 2-({6-[3-(1-hydroxypentyl)-1-benzofuran-2-yl]-1-methyl-2-naphthyl}oxy)acetonitrile was obtained as a yellow gum (0.838 g,). 1HNMR (300 MHz, DMSO-d6): δ8.3 (s, 1H), 8.15 (d, 1H, J=9.2 Hz), 8.0 (t, 1H, J=8.5 Hz), 7.9 (t, 1H, J=7.7 Hz), 7.55 (q, 3H, J=8.2 Hz), 7.25-7.35 (br, 1H), 5.45 (d, 1H, J=5.4 Hz), 5.35 (s, 2H), 5.1-5.2 (br, 1H), 2.55 (s, 3H), 1.8-2.0 (br, 2H), 1.2-1.3 (br, 2H), 1.35 (t, 2H, J=7.3 Hz), and 0.8 ppm (t, 3H, J=7.3 Hz).

Sources & evidence

ORD record
ord-9a9f02fc7b444dfc8a384e16a58c71fd
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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