Trifluoroacetic acid → HCID 66642661, compound

HRID 1170958Notes

Reaction equation

HRID 1170958 reaction equation
[CH3:1][C:2]1[C:7]([O:8][Si](C(C)(C)C)(C)C)=[C:6](Br)[C:5]([CH3:17])=[CH:4][C:3]=1O.[CH:19]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[O:30][CH2:31][O:32][CH3:33])[CH:25]=O)([CH3:21])[CH3:20].C(O)(C(F)(F)F)=O>CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:25][C:24]2[CH:27]=[CH:28][C:29]([O:30][CH2:31][O:32][CH3:33])=[C:22]([CH:19]([CH3:21])[CH3:20])[CH:23]=2)[C:5]([CH3:17])=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 86052179HCID 86052179, compoundHCID 87485710HCID 87485710, compound

Product 1

HCID 66642661HCID 66642661, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Intermediate 2,5-dimethyl-4-(3′-iso-propyl-4′-methoxymethoxybenzyl)phenol was prepared from 2,5-dimethyl-4-bromo-t-butyldimethylsilyloxyphenol, and 3-iso-propyl-4-methoxymethoxybenzaldehyde according to the procedure described in (G. Chiellini et al. Biorg. Med. Chem. Lett. 2000, 10, 2607) and transformed into the title compound by the procedure used for the synthesis of compound 7-13, step b followed by example 7, step b, (0.14 g, 90%); 1H NMR (300 MHz, CD3OD): δ 6.88 (d, J=8.7 Hz, 2H), 6.79 (s, 1 H), 6.64-6.72 (m, 2 H), 4.20 (d, J=10.2 Hz, 2 H), 3.80 (s, 2 H), 3.10-3.15 (m, 1 H), 2.22 (s, 3 H), 2.20 (s, 3 H), 1.17 (d, J=6.9 Hz, 6 H); LC-MS m/z 365 [C20H25O6P+H]+; HPLC conditions: ODSAQ AQ-303-5 column; mobile phase=CH3OH: 0.05% TFA (7:3) flow rate=1.0 mL/min; detection=UV@254 nm retention time in min: 10.96; Anal Calcd for (C20H25O6P+0.3H2O): C, 61.84; H, 6.92. Found: C, 61.60; H, 6.72.

Sources & evidence

ORD record
ord-f3b28e605c0c47fea33a87ae4034dd98
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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