Water → (3RS,4RS)-4-[8-(t-butyldimethylsilyloxy)octynyl]-4-hydroxy-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran

HRID 1859297Notes

Reaction equation

HRID 1859297 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]#[CH:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li]CCCC.[CH3:22][O:23][CH2:24][O:25][C:26]1[CH:47]=[CH:46][C:29]2[C:30](=[O:45])[C:31]([C:35]3[CH:40]=[CH:39][C:38]([O:41][CH2:42][O:43][CH3:44])=[CH:37][CH:36]=3)([CH3:34])[CH2:32][O:33][C:28]=2[CH:27]=1.O>O1CCCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]#[C:16][C:30]1([OH:45])[C:29]2[CH:46]=[CH:47][C:26]([O:25][CH2:24][O:23][CH3:22])=[CH:27][C:28]=2[O:33][CH2:32][C:31]1([C:35]1[CH:36]=[CH:37][C:38]([O:41][CH2:42][O:43][CH3:44])=[CH:39][CH:40]=1)[CH3:34])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 104217908-(t-Butyldimethylsilyloxy)-1-octyneHCID 154817637-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-oneHCID 178418339Butyllithium

Product 1

HCID 22123603(3RS,4RS)-4-[8-(t-butyldimethylsilyloxy)octynyl]-4-hydroxy-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyranYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

8-(t-Butyldimethylsilyloxy)oct-1-yne (0.6 g, 2.5 mmol) was dissolved in dry tetrahydrofuran (8 ml) under argon atmosphere and then cooled to -78° C. 2.5M n-BuLi (0.94 ml, 2.35 mmol) was slowly added dropwise thereto and then the mixture was stirred for 30 minutes. To the mixture was added dropwise 7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran-4-one (300 mg, 0.84 mmol) dissolved in dry tetrahydrofuran (4 ml), and then the reaction mixture was slowly warmed to room temperature. After 3 hours, water was added to the reaction mixture. The reaction solution was extracted with ethyl acetate and the organic layer was dried over magnesium sulfate. The residue was subjected to column chromatography (n-hexane:ethyl acetate=4:1) to obtain 500 mg (yield: ~100%) of the title compound as a colorless oil.

Workup

  1. temperaturethe reaction mixture was slowly warmed to room temperature
  2. waitAfter 3 hours
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over magnesium sulfate

Sources & evidence

ORD record
ord-8d64d086ad1c4364a5dd0021a691b4dd
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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