Methanol → 4-(2,2,4,4-Tetramethyl-8-prop-2-ynyl-chroman-6-ylethynyl)-phenyl-acetic acid

HRID 898679Notes

Reaction equation

HRID 898679 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[C:15]3[C:20](=[C:21]([CH2:23][C:24]#[C:25][Si](C)(C)C)[CH:22]=2)[O:19][C:18]([CH3:31])([CH3:30])[CH2:17][C:16]3([CH3:33])[CH3:32])=[CH:7][CH:6]=1.CO.O1CCCC1.O.[OH-].[Li+]>O>[CH3:30][C:18]1([CH3:31])[CH2:17][C:16]([CH3:32])([CH3:33])[C:15]2[C:20](=[C:21]([CH2:23][C:24]#[CH:25])[CH:22]=[C:13]([C:12]#[C:11][C:8]3[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:34])=[O:2])=[CH:10][CH:9]=3)[CH:14]=2)[O:19]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 69216503HCID 69216503, compound2×

Product 1

HCID 102873324-(2,2,4,4-Tetramethyl-8-prop-2-ynyl-chroman-6-ylethynyl)-phenyl-acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Following general procedure K and using {4-[2,2,4,4-tetramethyl-8-(3-trimethylsilanyl-prop-2-ynyl)-chroman-6-ylethynyl]-phenyl}-acetic acid methyl ester (Compound 48, 0.105 g, 0.21 mmol), methanol (3 mL), tetrahydrofuran (3 mL), water (1.5 mL) and lithium hydroxide monohydrate (0.128 g, 3.07 mmol), the title compound was obtained as a pale yellow solid (0.077 g, 95%). 1H NMR (300 MHz, CDCl3): δ7.51 (d, 1H, J=2.2 Hz), 7.49 (d, 2H, J=8.2 Hz), 7.39 (d, 1H, J=2.2 Hz), 7.25 (d, 2H, J=8.2 Hz), 3.66 (s, 2H), 3.52 (d, 2H, J=2.6 Hz), 2.61 (t, 1H, J=2.6 Hz), 1.83 (s, 2H), 1.36 (s, 6H), 1.35 (s, 6H).

Sources & evidence

ORD record
ord-7b89d6a853594c888727bbbb854db39b
Source dataset
uspto-grants-2008_04
Patent number
US07351737B2

Reaction notes

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