2-(3-Fluorophenyl)chroman-6-ol → 2-(4-Ethylphenyl)chroman-6-ol

HRID 31201Notes

Reaction equation

HRID 31201 reaction equation
FC1C=C(C2CCC3C(=CC=C(O)C=3)O2)C=CC=1.[CH2:19]([C:21]1[CH:26]=[CH:25][C:24]([CH:27]2[CH2:36][CH:35](O)[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([OH:38])[CH:33]=3)[O:28]2)=[CH:23][CH:22]=1)[CH3:20]>>[CH2:19]([C:21]1[CH:22]=[CH:23][C:24]([CH:27]2[CH2:36][CH2:35][C:34]3[C:29](=[CH:30][CH:31]=[C:32]([OH:38])[CH:33]=3)[O:28]2)=[CH:25][CH:26]=1)[CH3:20]

Participants

3

Reactant 2

HCID 179784712-(3-Fluorophenyl)chroman-6-olHCID 179785372-(4-Ethyl-phenyl)chroman-4,6-diol

Product 1

HCID 179784982-(4-Ethylphenyl)chroman-6-ol

Procedure

2-(4-Ethylphenyl)chroman-6-ol was prepared as described for 2-(3-fluorophenyl)chroman-6-ol in Example 9(c) starting from 425 mg of 2-(4-ethyl-phenyl)chroman-4,6-diol. The product was purified using heptane-ethyl acetate (3:1) as an eluant. 1H NMR (400 MHz, CD3OD) δ: 7.26 (d, 2H, J 8.2 Hz), 7.13 (d, 2H, J 8.2 Hz), 6.65 (d, 1H, J 8.6 Hz), 6.55 (dd, 1H, J 8.6, 2.8 Hz), 6.51 (d, 1H, J 2.8 Hz), 4.83 (dd, 1H, J 10.1, 2.3 Hz), 2.84 (m, 1H), 2.62 (m, 1H), 2.59 (q, 2H, J 7.6 Hz), 2.03 (m, 1H), 1.93 (m, 1H), 1.19 (t, 3H, J 7.6 Hz).

Workup

  1. customThe product was purified

Sources & evidence

ORD record
ord-291699fe3029458698307735d25b3af0
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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