Hydrochloric Acid → 5-Iodo-2-(2-methoxy-ethoxymethoxy)-benzyl alcohol

HRID 1636775Notes

Reaction equation

[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:5]=1[CH:6]=[O:7].[CH3:13][O:14][CH2:15][CH2:16][O:17][CH2:18]OCl.[BH4-].[Na+].Cl>C1COCC1.O.CCOCC.CN1CCCN(C)C1=O>[I:12][C:9]1[CH:10]=[CH:11][C:4]([O:3][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:5]([CH:8]=1)[CH2:6][OH:7]

Participants

Conditions

Temperature: -15 °C

Procedure

To a solution of sodium hydride (1.2 g of a 60% mineral oil dispersion, 52 mmol) in 25 mL of THF at 0° C., is added 2-hydroxy-5-iodo-benzaldehyde (7.0 g, 28 mmol). To the resulting solution is added 2-methoxy-ethoxymethoxy chloride (3.4 mL, 30 mmol) and 4 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone. The solution is allowed to warm to ambient temperatures. After 45 minutes, the solution is cooled to -15° C. and 6 mL of a 2 M solution of sodium borohydride in THF is added. The solution is stirred for 10 minutes. After this time, 24 mL of a 2M HCl solution in water is added. The resulting solution is diluted with ether, washed with water and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The resulting crude material is purified by column chromatography eluting with 40% EtOAc/hexanes to give the title compound (7.6 g, 22.5 mmol) as a white solid.

Workup

temperatureto warm to ambient temperatures
washwashed with water and saturated NaCl
dry with materialThe organic layer is dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe resulting crude material is purified by column chromatography
washeluting with 40% EtOAc/hexanes

Sources & evidence

ORD record: ord-0c89c3bf1c9040949e735c9eb04edf2b
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06034093

Reaction notes

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