HCID 66642817, compound → HCID 66642767, compound

HRID 2108603Notes

Reaction equation

HRID 2108603 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([O:10][Si](C(C)C)(C(C)C)C(C)C)[C:7]([CH3:21])=[CH:6][C:3]=1[CH:4]=O.Br[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([CH:31]([CH3:33])[CH3:32])[C:24]=1[CH3:34]>>[CH3:21][C:7]1[CH:6]=[C:3]([CH2:4][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([CH:31]([CH3:32])[CH3:33])[C:24]=2[CH3:34])[C:2]([CH3:1])=[CH:9][C:8]=1[OH:10]

Participants

3

Reactant 2

HCID 66642817HCID 66642817, compoundHCID 860521872,5-Dimethyl-4-triisopropylsilanyloxy-benzaldehyde

Product 1

HCID 66642767HCID 66642767, compound

Procedure

Intermediate 2,5-dimethyl-4-(4′-methoxy-2′-methyl-3′-iso-propyl-benzyl) phenol was prepared from 2,5-dimethyl-4-triisopropylsilanyloxy-benzaldehyde and 1-bromo-4-methoxy-2-methyl-3-iso-propylbenzene according to the procedure described in Chiellini et al., Bioorg. Med. Chem. Lett. 10:2607 (2000) and transformed into the title compound by the procedure described for the synthesis of compound 7: 1H NMR (300 MHz, DMSO-d6): δ 6.93 (s, 1H), 6.75 (d, J=8.4 Hz, 1H), 6.65 (d, J=8.4 Hz, 1H), 6.64 (s, 1H), 4.09 (d, J=9.9 Hz, 2H), 3.79 (s, 2H), 3.77 (s, 3H), 3.34 (m, 1H), 2.22 (s, 3H), 2.20 (s, 3H), 2.10 (s, 3H), 1.31 (d, J=7.2 Hz, 6H); LC-MS m/z=391 [C21H29O5P−H]−.

Sources & evidence

ORD record
ord-0241f8a8b26f4e54aaec3c8905f29466
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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