Water → HCID 22033136, compound

HRID 1792334Notes

Reaction equation

HRID 1792334 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][O:17][CH3:18])=[CH:12][CH:13]=2)[O:8][CH2:7][C:6]1([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][O:28][CH3:29])=[CH:22][CH:21]=1)[CH3:19].[CH3:30][S:31](Cl)(=[O:33])=[O:32].C(N(CC)CC)C.O>ClCCl.C(OCC)(=O)C.CCCCCC>[CH3:30][S:31]([O:1][CH2:2][CH2:3][CH2:4][CH:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][O:17][CH3:18])=[CH:12][CH:13]=2)[O:8][CH2:7][C:6]1([C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][O:28][CH3:29])=[CH:24][CH:25]=1)[CH3:19])(=[O:33])=[O:32]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22033053HCID 22033053, compound

Product 1

HCID 22033136HCID 22033136, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(3-Hydroxypropyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (280 mg, 0.70 mmol) was dissolved in dichloromethane (50 ml), methanesulfonylchloride (0.32 g) and triethylamine (0.30 g) were added thereto, and the mixture was stirred at room temperature for 1 hour After the reaction was completed, the reaction mixture was poured into water and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a crude product. This crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=3:1) to give 4-(3-methanesulfonyloxypropyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (a mixture of (3RS,4RS) and (3RS,4SR), (3RS,4RS)/(3RS,4SR)=about 6/1) (350 mg, stoichiometric yield). Then, to a solution of the product (0.59 g, 1.2 mmol) in DMF (15 ml) was added sodium azide (0.14 g), and the mixture was stirred at 60° C. for 2 hours. After the reaction was completed, the reaction mixture was poured into water and extracted with ether. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a crude product. This crude product thus obtained was subjected to preparative TLC (n-hexane/ethyl acetate=10/1 for twice, 5/1 for twice) to produce (3RS,4RS)-4-(3-azidopropyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-m ethylchroman (220 mg, yield 42%).

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a crude product
  5. customThis crude product thus obtained

Sources & evidence

ORD record
ord-5016be00e95248d5807a0304abc59a13
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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